


A Long Walk Off A Short Pier

by DarknessBound



Series: FireworksFest [1]
Category: Supernatural
Genre: Alternate Universe - High School, Angst with a Happy Ending, Arrogant Dean Winchester, Bottom Castiel/Top Dean Winchester, Castiel's First Kiss (Supernatural), Castiel's First Time Having Sex (Supernatural), Cute, Embarrassed Castiel (Supernatural), Enemies to Lovers, Eventual Happy Ending, Eventual Smut, Falling In Love, Flirting, M/M, Prom, Promposals, Romantic Gestures, Slow Burn, both are eighteen, idiots to lovers
Language: English
Status: Completed
Published: 2020-07-03
Updated: 2020-07-05
Packaged: 2021-03-04 19:00:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 10
Words: 21,553
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25051318
Author URL: https://archiveofourown.org/users/DarknessBound/pseuds/DarknessBound
Summary: Dean loved to procrastinate, and finding himself a prom date was no exception. Being one of the most popular guys had its perks - he quite literally bet Jimmy Novak he could get anyone he asked, no matter when he asked them. But when Jimmy called his bluff and set Dean’s sights on his twin brother, Cas, Dean found out that at least one person at Brinetide High was seemingly immune to his charms.
Relationships: Castiel/Dean Winchester
Series: FireworksFest [1]
Series URL: https://archiveofourown.org/series/1911268
Comments: 78
Kudos: 300
Collections: The Destiel Fan Survey Favs Collection





	1. The Bet

**Dean**

“Oh, look what the cat dragged in.” Jask had his arm around his boyfriend, Ares, on the couch, a huge grin on his face.

Dean scoffed. “No cats. I’m allergic.” He plopped his ass down next to the happy couple and unwrapped his burrito, taking a huge, obnoxious bite while Ares looked at him like he was a martian. “What?” Dean mumbled with his mouth full.

“You’re disgusting.” He turned the other way with an eye roll and nudged Jask when he laughed. Ares was alright. He didn’t play football with them, but he and Jask were pretty damn cute if Dean was being honest. He’d never seen J this happy before. 

Jask was actually Dean’s first kiss back in the seventh grade, and they had helped each other come out the following year. They both instantly realized after that one kiss that they were meant to just be friends, and having a best friend on that journey - right next to him - had been awesome for Dean. He wasn’t sure if he would have had the balls to be so  _ out _ if it wasn’t for him. 

Jimmy helped, too. He was the straight one in their crew, but he never shamed them. The three of them were pretty inseparable since elementary school, and Dean was sure being around them all these years helped Jim when his twin brother came out sophomore year. He occasionally joked about how he was surrounded by gays, but Dean could tell he didn’t mind, especially when he often said, “more chicks for me.”

Dean kept eating his burrito in peace as more people showed up at Jask’s parents’ house. They went out of town often, and now that they were all seniors, they didn’t mind the parties - as long as no one broke anything or got the cops called. 

“Dean-o!” Jimmy called out as he walked in. “Always eating, huh?” He walked over and sat in the recliner. “You bring one for me?”

“Pfft, no.” He took another bite and smiled like an asshole.

“Whatever. You got a date to prom yet, Winchester?”

Dean rolled his eyes and kept eating without a care in the world. Before he could respond, Jask spoke up. “Dean doesn’t have a date?” He saw Ares head turn quickly, wanting to know the answer, too.

“Well… no. Not exactly. But I could get one if I wanted. I don’t even know if I’m going.”  _ Drop it, asshats.  _

“Pretty much everyone has established who they are going with, Dean. You should decide soon, before you end up dateless.” Ares stated.

_ Thanks to Captain Obvious here.  _ It wasn’t that Dean was nervous to ask anyone, he knew  _ whoever _ he asked would say yes; he was Dean fucking Winchester. “Look, I’m not worried about it. I could ask them the day of and they’d say yes.”

“Cocky, are we?” Jask leaned forward. “And who are you thinking, exactly?” 

“No one… yet. But it doesn’t matter. Whoever the hell it is would say yes. If I even wanted to go, and I probably won’t. The theme is stupid.” 

_ “‘Whoever the hell’ _ really, Dean?” Jimmy laughed like he doubted him.

Dean finished his burrito and narrowed his gaze. “You doubt me? Name one damn gay dude that would deny me.” He brushed his hands together.

“Well, me.” Ares said and Dean rolled his eyes. 

“You don’t count. You have a boyfriend.” He deadpanned and turned back to Jimmy. “Come on, someone else.” 

Jimmy scoffed and took a moment to think with his head cocked to the side. He shrugged after a while and huffed a laugh. “My brother.” 

_ Okay, that was unexpected.  _ “You said he was off limits last year.” 

Cas was… a nerd, to say the least. And aside from his best friend, Kevin, he didn’t hang out with anyone. He and Jimmy were twins, but they couldn’t be more different. 

“Yeah, he was fragile last year. This year he’s pretty damn confident in himself, and will 100% tell you to fuck off.”

Dean frowned. “Pfft, fuck off?  _ You _ can fuck off with that nonsense. I’ve caught him checking out my ass.” It was a lie, not that Jimmy knew that.

His laugh at that was obnoxious. “Sure you did. I bet he tells you no before you finish the question.”

_ Challenge accepted, douchebag.  _ “You’re on, Jimbo.”  _ Won’t even need to be a question. I’m fucking lovable. _

“Cas denying you is going to be the highlight of my high school career, I just want you to know that,” Jimmy said, still smiling like a dick. “This is gonna be great.”

Dean shrugged with a cocky grin. “I’m not worried at all. Ima make his ass swoon, just watch.” He sat there thinking of a bunch of extravagant ways to ask, just to make a show of it and ultimately decided on just telling him when he’d pick him up.  _ Why make it complicated?  _

Jimmy rolled his eyes. “I don’t think Cas has swooned over anything since the news that there was a 7th Star Wars coming out. Good luck… and make sure I’m there to watch.” 

“Star Wars? He must have good taste.”  _ Now I know he’ll say yeah. _ “I’ll ask him Monday morning.”

“Suit yourself, it’s your funeral.”

~~~~

When Dean laid in bed that night, he suddenly wasn’t so sure. Cas was hot, no denying that, but the dude had never given any signs he was even remotely attracted to Dean. 

He had assumed it was because he was friends with Jimmy, but what if he just legitimately didn’t like Dean? Pretty much every jock heard the bet, and he wasn't sure if he could handle that level of rejection.  _ Nah, you got this. You can be charming when you want.  _ He laughed at himself for even doubting Cas would say yes. Of course he would. Dean was the hottest guy at school - hell in the whole town. Cas should be friggin honored. 

By the time he fell asleep that night, Dean had gained all his confidence back and slept like a baby. Come Monday, he’d have a prom date and everyone would shut the hell up about it. 

What could go wrong?

**Castiel**

The only thing more annoying than prom, were people  _ going  _ to prom. If Cas was being honest with himself, even the people that  _ weren’t  _ going were irritating. No matter what their status was, no one seemed to be talking about anything at all but that stupid dance.

Maybe he was just upset that the event was less than a month away and no one had asked him, but that fact didn’t surprise him in the least. His twin brother got all the charisma and athletic talent in the family, and as high school cliques go, that pretty much left Cas in the dust. 

His one and only friend nudged him, bringing him back to reality. “Will you stop thinking about it? It’ll be here and over soon, then people can go back to talking about  _ other  _ boring things.” 

_ Easy for you to say, you have a date.  _ “Who said I was thinking about it?”

Kevin raised his eyebrows. “Are you kidding? It’s practically written on your forehead. Why don’t you just ask Balt?”

“He has a date. Not that I’d ask him - or  _ anyone -  _ anyway.”

“Okay, what about Charlie?”

_ Is he not hearing me?  _ “I barely know her, but I know enough to know that we bat for very different teams. Also, I’m fairly certain that she, too, has a date already. Can we drop this? I don’t want to go.”

And he didn’t, for about a thousand reasons. Not having a date was just one of them. Kevin just sighed like Cas was inconveniencing him, and made his way to his first period class, leaving Cas to his thoughts. 

Walking into History, Cas could immediately tell something was weird. His brother was having a hushed, heated conversation with Brinetide’s pompous safety…  _ something  _ Winchester. Cas probably should remember his name, he’d been friends with Jimmy since they were kids, but Cas made a point not to save room in his brain for assholes. 

And whatever his name was, the guy was an asshole.  _ The hot ones always seem to be.  _ Cas set his books down as the bell rang, and Jimmy came over to sit next to him. 

“Hey, little bro! How are you this fine morning?” Jimmy grinned like he knew a secret, making Cas nervous.

Cas eyed him as he opened his book. “I’m fine. Why are you being… suspicious?”

“Why are you paranoid?” Jimmy sat back and Cas could see Dean on the other side, watching him with a weird expression.

_ Dean, that’s his damn name. Dean.  _ Cas huffed, glad it came to him, but still wary of whatever it was the two of them had been talking about. “I’m not paranoid, I’m your twin. I think I’ve learned over the years how to pick out when you’re up to something.”

Jimmy laughed and the teacher started talking, but he leaned over. “Still not wanting to go to prom?”

A terrible sense of foreboding washed over him, but he kept his face as neutral as possible. “Of course not. I’ve been telling you since we learned what it was that I wasn’t interested, nothing has changed. So don’t get any stupid ideas.” He flicked his eyes to Dean again, and found him still staring.  _ Shit.  _

Their eyes met for a brief second before Dean finally turned towards the teacher, but he still wearing that agitating smirk. 

Jimmy leaned over and blocked him from view. “I don’t have any dumb ideas. I was just curious, Cassie boo.”

“Don’t call me that.” Cas slunk down in his seat and turned his attention toward Mr. Cain, fidgeting every few moments because he could  _ feel  _ someone staring at him. 

His notebook was unusually lacking in notes when the bell rang, but Cas figured he’d either get them from someone else or just go talk to Cain during his free period. He wasn’t sure what he’d use as an excuse -  _ ‘oh, yes, I was there. I just wasn’t listening, because my twin brother is a notorious instigator and I spent the entire class wondering what fresh hell was awaiting me. Sorry, can you repeat the entire class for me?’  _

Something about his teacher’s general demeanor told him that wouldn’t be taken kindly, so Cas would have to settle for reading back over the chapter a hundred times. He gathered his things and was just about to leave when Jimmy threw his hand up and pointed behind him. 

Cas turned to see Dean walking up - stopping  _ much _ too close - with his tongue between his lips. “Hey, Cas. So... you… me… prom.”

There it was. That explained Jimmy’s weirdness and the looks Dean had been giving him, but nothing in the world could explain  _ why  _ it was happening.  _ This has  _ **_got_ ** _ to be a joke. This is a joke, they’re doing it to make fun of me.  _ He’d expect such a thing from Dean, but not from his twin. It stung in ways he didn’t want to think about. 

He realized then that Dean, along with several others, were waiting for an answer. “Um… no, thank you.”

Dean laughed, and looked around at the few people watching. “You’re funny. I’ll pick you up at 7.” 

“Dean, I said no.” Cas shifted, his mind working overtime to try and connect the dots. The only thing that made any sense was that Jimmy put him up to it for some reason, and Cas was  _ not  _ a joke. 

“What, you’ve already got a date?”

_ I bet you know I don’t.  _ Cas blushed, his cheeks blossoming with unwanted, traitorous color as the embarrassment of being used as a punchline kicked in. “No, I just don’t want to go with  _ you.”  _

The look on Dean’s face was a mix between shock and disbelief, and Cas could hear Jimmy laughing as he walked away, leaving Cas standing awkwardly in front of Dean. 

He didn’t say another word, he turned on his heel and exited the room so quickly, he shoulder-checked the doorframe. 

_ What the fuck was that? _


	2. The Denial

**Dean**

Dean thought this was some kinda joke and stared after Cas, scratching his head. Jimmy thought this was funner than the time Jask ripped his pants and when Cas was finally out of view, he turned to find his traitorous friend. “You cheated. Did you pay him to say no?”

“Didn’t have to. My brother can smell bullshit from six miles away, and you reek of it, Dean-o.” Jimmy cackled, smacking Dean’s shoulder. “I win.”

“Hell no, you don’t. I’m not givin’ up. He just has to know I mean it.” Dean wasn’t about to lose this dumb bet. He and Cas were... almost friends... right? Why would he say no? “I just gotta up my game a little, it’s fine. I got this.”

Jimmy shrugged, not seeming concerned in the slightest. “Yeah, whatever. He’ll just have to find more ways to say no then, which I doubt’ll be a problem.”

Dean rolled his eyes and pulled Jimmy aside, away from the other jocks. “No really, does he not like me?”

“He hates you, judging by the look on his face... he’s never mentioned you, though.” Jimmy clicked his tongue and pushed Dean’s hand off of him. “Not everyone has to like you, Dean. Good for my brother for being the one person in all of Brinetide that doesn’t.”

“Whatever. Everyone likes me. I’m not a dick like you.” He ruffled Jimmy’s short hair and walked off. 

By the end of the day, Dean was actually worried Cas might just hate him. He definitely avoided him all day and even though they had lunch and fifth period together, Dean didn’t get one opportunity to talk to him. Cas even somehow found a way to leave class three minutes early and was nowhere to be found. He slipped a note with his phone number in Cas’ locker asking again, and also went out of his way to bribe the cheerleaders to help him decorate it. Dean wrote ‘prom’ on so many heart cutouts his hand hurt, but in the end, it looked awesome. The streamers could be seen from down the hall and he couldn’t help but laugh at how ridiculous he was starting to feel. Maybe he’ll at least text. 

He didn’t. Good thing about knowing the Novaks so long was that he knew Cas always went on a jog in the evenings, so he made his way over, running along the trail he hoped Cas would take. 

It took longer than he’d admit, but he finally saw Cas jogging down the street. He tried not to startle him, and based on Cas’ reaction, he failed. “Hiya, Cas! Oh shit, I didn’t mean to scare you.” He flashed a smile and checked him out. Dude really is hot, much hotter than Jimmy.

Cas just kept running, barely sparing him a second glance. “What do you want?”

So Dean ran along with him. “Just wanted to say hi. And ask why you said no.”

“Why do you even care? Did I bruise your ego?” Cas rounded a corner, gaining a couple of steps on him. “I just don’t want to go with you, or anyone else.”

“Why not? Prom is...” _Stupid._ “a rite of passage.” Dean rolled his eyes at himself and caught up. “You did bruise my ego, actually. But, I realize I didn’t technically ask you. So, Castiel. Will you go to prom with me?”

He slowed to a stop, his cheeks almost as red as they had been the first time. Cas ran a hand through his sweaty hair and narrowed his eyes at Dean. “Okay, I guess I’ll say it again. No. Ask someone else.” He took off again, heading back the way he came.

Dean watched him go, but didn’t follow this time. He got it now, Cas wanted to be romanced. “Oh, I’ll romance the hell outta you, Cas!” He called out with a grin. “Just wait.”

Cas faltered for a couple of steps, shook his head without looking back, and kept going. 

Dean walked home, trying to figure out what Cas might like. He knew he liked Star Wars... but that was about it. Maybe Jimmy could help? He sent him a quick text while he ran up the stairs to his bedroom.

**Dean: _Hey, your brother wants me to woo him. What are some things he likes?_**

He set his phone aside and started writing a list of ways he could ask. Within minutes, most were crossed out but he had a few good ideas, he just had to pick one.

**Jimbo: _Yeah, I don’t think he wants that. But if you insist, he enjoys really big gestures. Think… writing his name in the sky type shit. The more people around, the better._**

**Dean: _Knew it! I got this_**

He chuckled and made a new list. Dean got along well with the principal and was sure he’d let him ask Cas to prom with the intercom. More people the better, how about the whole damn school. Dean went to bed that night, without a shadow of a doubt that he’d have Cas as a prom date by the morning. 

The next day, Dean had donuts that spelled ‘PROM?’ delivered to Cas’ first period desk just as the announcements started. Convincing the principal wasn’t too hard - especially since Dean brought her a donut - but he had to promise not to play any games with the intercom. He could ask Cas to prom, and then get to class - that’s it.

“Uh... testing is this thing on? Testicles? Okay no, no m’sorry I won’t play anymore.” Shit, I almost got cut off! “Um, Castiel Novak? This is Dean Winchester, your prom date, even if you keep saying no. You didn’t call last night. So, now I have the big sad. Let’s try this again. Will you go to prom with me? Text me, cause I know you got my number. Winchester, out.” 

Everyone in the office was smiling at him and it made him blush. “He’s gonna say no again. But ima keep trying.”

**Castiel**

Every single pair of eyes was trained on Cas, and he wanted to die. What in the hell is happening? This can’t be my life. That familiar warmth flooded his face as his classmates started saying things like ‘you’re gonna say yes, right?’ and ‘I didn’t know Winchester was into nerds.’

_He’s not, he’s only acting like it because… because… shit. I honestly have no idea. It’s gone on long enough now that I’m going to have to ask Jimmy when I get home. If he really did have something to do with it, maybe I can make it stop before things get even more out of hand._

Cas made himself as small as he could and ignored the comments still being made around him as he pulled out the note Dean had left in his locker the previous day. He quickly input the number into his phone and sent him a simple text.

****

**Castiel: _I didn’t call because I have nothing new to say. The answer is still no._**

He pushed himself out of his seat and slung his bag over his shoulder as he made his way to first period, already dreading it. As if it wasn’t bad enough on a normal day, now he was going to have to deal with Dean and a room full of Dean’s friends asking him why he said no. 

There was a box of donuts on his desk, and Cas briefly considered skipping the class altogether - but they had a test coming up and he’d already missed a big enough chunk thanks to Dean. 

Reluctantly, he opened the box. A couple of kids sniggered when they peeked over his shoulder, and Cas was nearing the end of his rope. He took a huge bite of the P, then bit the last line of the M off to make it an N. He gave the R to some girl he barely knew and rearranged what was left to spell ‘NO,’ then put the box on Dean’s desk and returned to his seat, casually enjoying the rest of the one he’d saved.

Dean walked in the classroom with an annoying grin. Kids were teasing him, right to his face and it didn’t even remotely faze him. How could someone be so full of themselves? He only faltered slightly when he saw the box on his desk but quickly shrugged it off. “Still not good enough? Alright then, Cas.” He sat down and opened the box, glancing over with an amused smile. Cas blushed when their eyes met and the fucker winked, seconds before shoving practically the entire ‘O’ into his mouth.

For the first time, Cas briefly considered saying yes. Not because he actually wanted to go to prom or believed Dean wanted to go with him, but because he desperately wanted to know what else his mouth could do. He’d be an idiot - and a blind one at that - not to notice how insanely, unreasonably attractive Dean was. _Shit. This is not the time, and Dean is not the type of boy I should be thinking about._

Dean ate the donuts, not even pausing on the one Cas had previously bitten, and then pulled out his phone. Before Cas’ phone vibrated, he already knew who it was. 

**Dean: _A New Hope or Return of the Jedi?_**

Cas spared a moment to feel bad for Mr. Cain, he had no doubt in his mind that kids rarely paid attention to him despite his commanding nature and interesting subject. He flicked his eyes from the board to his phone, and decided not to respond. _Whatever game this is, I’m not playing._

Class droned on, and Cas became more fidgety by the second. The more he tried to convince himself not to respond, the more he actually wanted to, until the urge wasn’t something he could keep ignoring. Okay. _Just once, simply because the question was ridiculous and I can’t have him walking around believing the wrong answer._

**Cas: _For nostalgia purposes, A New Hope. If we’re talking content and cinematic mastery, Return of the Jedi._**

His phone vibrated before he could pick up his pen.

**Dean: _Agreed. Do you think Vadar’s character was redeemable?_**

The question caught him off guard in a way few things ever did. But, he was beginning to suspect that was just Dean. 

**Cas: _Yes, I do. But then again, I think everyone is redeemable, given enough time and the correct circumstances._**

****

**Dean: _Everyone huh? What about a jock?_**

_Damnit. I should have seen that coming._ Cas glanced behind him to look at Dean, but for once, Dean wasn’t looking back. He was staring at his lap with his lip tucked between his teeth and his eyebrows pinched, like he was genuinely concerned about what Cas was going to respond. 

On principle alone, Cas nearly ended the conversation there. People like Dean were attention-seekers to the core, and Cas had little doubt that Dean only wanted validation because Cas denied him. 

**Cas: _Are you honestly comparing yourself to one of the most recognizable villains of all time? Interesting._**

It actually wasn’t interesting, it was weird, but Cas didn’t feel like having that argument. Normally jocks saw themselves as some kind of heroes, put here to save the school from athletic embarrassment or something equally cliché. He certainly never thought Dean would even come close to admitting he was less than perfect, and because of that, Cas was becoming even more confused. 

_Maybe I’m overreacting? Maybe he’s not like all the others, and I should’ve said yes?_

He still had the thread open, so his phone didn’t even buzz as the back-to-back responses came in. 

**Dean: _Not at all. YOU said everyone. Plus I’m not a villain._**

****

**Dean: _I’m more like Batman._**

And just like that, nearly every ounce of curiosity Cas had about Dean vanished. Of course he thinks he’s Batman, how could I possibly have thought otherwise? He shook his head, tucking his phone away and propping his chin on his hand, wondering how the hell he could ever be dumb enough to think Dean was anything more than a meathead. 


	3. The Thawing (Of Ice)

**Dean**

Once again, Cas was ignoring him. He wasn’t sure where he fucked up there. He had thought their conversation was going well and then he just stopped responding. 

**Dean:** **_Alright then, guess everyone is redeemable but me. You’re making this very difficult. Can’t we just be friends?_ **

The bell rang when Cas was still typing, and the moment he finished, he dashed out the door just as the message came through. 

**_Cas: You have had twelve years to be my friend, Dean. Forgive me if I’m finding it hard to believe you want to start now._ **

Dean sighed and ran a hand down his face.  _ This is not going well. What is it gonna take? _ Cas saying no so many times made him wanna back out of that stupid bet, but Jimmy’s dumb face convinced him to keep going. “You said the more people the better. That was the whole school.”

“He’s probably just testing you. Y’know, to make sure you really want it.” Jimmy was grinning from ear to ear, then snatched up the empty donut box. “If you want to quit, all you gotta do is admit there’s someone that won’t say yes to you. Then you can ask who you  _ really  _ want to ask.”

“Shut up.” Dean jumped up and started texting again.

**Dean:** **_People change_ **

He pocketed it and walked to his next class. People made jokes and laughed, but Dean didn’t care. They all wished someone would put this much effort into their promposal.  _ Asshats. _

**Cas:** **_Have you? Genuinely? Because the last time you spoke to me, it was roughly sixth grade and you were telling me about the ‘kick me’ sign that was on my back - which YOU put there._ **

_ Ah, fuck! _

**Dean:** **_Look, that was there for two seconds. I instantly regretted it._ **

Dean had completely forgotten about that dumb sign. That was another dare, and he hated himself for it. 

**Dean:** **_Sorry about that. I don’t think I ever apologized_ **

_ Yeah, definitely never said sorry. _

**Cas:** **_Apology accepted, can we move on now?_ **

**Dean:** **_Yeah. Prom?_ **

**Cas:** **_The answer is still no._ **

_ Well shit. A guy could dream. _ Dean shrugged and went to class, trying to think of another question to get Cas talking again. 

**Dean:** **_Who would you rather have, R2 or BB8?_ **

**Dean:** **_There is only one right answer here._ **

It worked, because his answer came almost immediately. 

**Cas:** **_R2D2. I don’t care how cute BB8 is._ **

**Dean:** **_Knew you had good taste._ **

He sat in class with a grin, feeling like he was getting somewhere. 

**Dean:** **_What else you like?_ **

**Dean:** **_DC or Marvel?_ **

**Cas:** **_DC, but don’t judge me. I’ve barely seen any of the Marvel movies and I was never into comics. Now, I’m trying to pay attention to class. Maybe you should. too._ **

Dean rolled his eyes and pocked his phone. He needed to think of his next plan anyway, and as soon as Charlie walked in, all he could think about was coffee. She worked at the small shop down the street and over time, she just made Dean crave coffee.

She always sat next to him in this class, so the second set her binder on the desk, he turned to face her. “Hey, Chuckles. What’s Cas’ usual drink?”

“Uh… Novak?” She squinted at him, taken aback by the question. “It depends on the day, but usually an Americano with an extra espresso shot. Why?”

“Because I’m gonna bring him coffee tomorrow.”  _ Duh. _ He pulled out his phone and typed his drink in the notes so he wouldn’t forget. “He’s gonna say yes soon, I can feel it.”

Charlie nodded slightly. “Uh  _ huh.  _ Why are you so interested in Cas all of a sudden?”

Dean contemplated his answer. Was it really about the bet anymore? Was it just because he was the first person to ever deny him? Was it because of his eyes? Dean wasn’t sure anymore. “I dunno. I just think he should go to prom and he won’t go. He’s gonna miss out.”  _ Lame, but maybe she’ll buy it. _

“So are you, if you don’t quit fighting a losing battle and just ask someone else.” She pulled out her book and flipped it open, scanning for the right page. “I don’t think he’s even had his first kiss yet, there’s no way he’s going to go with someone as…  _ experienced _ as you.”

“Experienced? What do you know about my  _ ‘experience’ _ huh?” Dean watched her, wondering just how much shit got around school. And was that even true? Could Cas have  _ seriously _ never kissed someone?

She shrugged, pointing up at the board to show him class had started. “I know enough, and so does everyone else.”

“Whatever. I’m innocent.” Dean turned to look up at the teacher with his arms crossed. He was definitely far from innocent, but he was never one to kiss and tell. Especially since a few were still in the closet. 

He hardly listened to the teacher, he was distracted by the thought of Cas never having kissed anyone before.  _ We’re seniors! Hasn’t everyone been having sex since like freshman year? _

Before he knew it, the bell rang and he was walking to his next class in a daze. Jimmy caught up with him in the doorway and snapped his fingers in front of Dean’s face to snap him out of it. 

“Earth to Dean-o. You okay in there?”

“Huh? Yeah. Hey, has Cas really never kissed anyone before?” Dean asked bluntly, realizing a little too late that he probably should have asked at a different time.

Jimmy’s face fell a little bit. “No, he hasn’t. It’s a sore subject for him, who the hell told you?”

“I was just told that it was a rumor. And that everyone thinks I’m a slut.” He rolled his eyes. “Whatever, rumors are stupid.”

He nodded, stepping in front of Dean to keep his attention. “Listen, Winchester. I’m not kidding, do whatever the hell you want with this promposal thing but do  _ not  _ \- I repeat, do  _ not -  _ embarrass him over this. And more importantly, don’t kiss him just because you think he needs it. Keep your damn lips off my brother, he deserves that shit to actually mean something.”

Dean frowned and held his hands up. “I wasn’t gonna violate him. Jesus.” He walked past him with a scoff.

All that bullshit did was fuck up his day. He spent the rest of his time at school lost in his own thoughts and avoiding everyone. He nearly backed out of his latest idea to ask Cas but felt obligated to follow through. Dean could feel the ice melting with Cas, he couldn’t quit now.

After the last bell, he made his way to the student center to print 300 flyers, and with Charlie’s reluctant help once again, they actually looked pretty awesome.

**Castiel**

Jimmy was acting weird again that night, but Cas chalked it up to instigator's remorse.  _ Good, I hope you regret it. It’s already insane.  _

Cas got ready for school the next morning, grateful it was finally Friday and he only had to suffer through one more day of Dean’s shenanigans.  _ Maybe I’ll get lucky and he’ll take the day off.  _

When it was time to leave, he couldn’t find Jimmy anywhere. Frowning, he grabbed his bag and considered texting Kevin for a ride, but didn’t want to be late. Cas had just decided to drive himself and opened the door to leave when he came face to face with Dean Winchester.

On his porch. 

At 7 am. 

“Jimmy apparently already left.”

“Yup. Mornin’ sunshine, coffee?” He handed him the drink with a huge grin. “I’m your ride.”

Cas sniffed it, smiling despite himself at the delicious aroma. “Thank you, Dean. This was… hold on.” He took a sip, feeling the warmth spread down his throat into his gut. It was perfect, exactly the way he liked it. “Is this a bribe? Are you bribing me with espresso?” 

“No. I’m just bringing you coffee and giving you a ride to school. Can’t a guy just be nice?”

_ Not in my experience.  _ Cas took another sip and shut his door behind him, flat out ignoring the butterflies somersaulting around inside of him. “Of course you can, I just… never knew that was a thing you enjoyed.” 

“I’m always nice, Cas. I joke around a lot, but I don’t bully people. That’s never been me, not since I put the dumb note on your back and felt like shit.” Dean walked to the passenger side and opened the door for Cas.

He honestly wasn’t sure whether to be offended or flattered by the gesture, but the immature, naive part of him was firmly on the side of flattered and couldn’t possibly be reasoned with. Cas sat, carefully holding his coffee so it wouldn’t spill. “Well then, I’m glad I played a role in steering you away from a life of crime.”

Dean closed the door and walked around, not commenting back. The rumble of his car made Cas jump slightly and Dean’s smile returned. “She won’t hurt you.” He pet the dash.

“Of course it won’t, it’s a car.” Cas swallowed, annoyed at himself for jumping. “It’s a really nice car, actually. I’ve seen it around, I guess I just didn’t realize it was yours.”

“Yup. I built her with my dad. Took a few years and a lot of busted knuckles, but it was worth it.” He pushed in some cassette tape and started driving without a care in the world.

Cas found himself staring at Dean more than usual as he sipped his coffee. He’d never noticed the freckles lining his cheeks and nose, but up close? He wasn’t sure which he liked better, those… or the flecks in his eyes. 

Yet again, he cursed himself for even trying to think of Dean like that. Just because spending time with him wasn’t as horrible as he thought, that didn’t mean Dean wasn’t trying to make a fool out of him. 

He was too chicken to ask again why Dean was asking him to go to prom, so he stayed silent until they pulled into the school’s parking lot. He looked over, keeping his eyes somewhere around Dean’s chest. “Thank you for the coffee, the ride, and… the concert.”

“Welcome.” Dean sat there a second, staring at Cas before he moved to get out of the car. “See you in first period, Cas.” He turned and offered a head nod with the most attractive smile Cas had ever seen, before he walked away.

For one, single moment, Cas closed his eyes and allowed himself to pretend it was real. That by some, weird twist of fate, someone like Dean was  _ actually  _ interested in someone like him. 

But life wasn’t a fairytale, and even if it was, Cas was far from a princess. He shook his head to clear his thoughts and walked into the building, but was stopped about a half a dozen times by people shoving papers into his hands.

When he reached his locker, he finally took a second to see what they were. The cover said nothing but ‘Urgent!’, and the inside read ‘Castiel, will you go to prom with me?’. 

_ And he said it wasn’t a bribe. What an ass.  _ He scoffed, opening his locker, but about fifty more of those flyers cascaded out onto the floor at his feet. 

He gathered up as many as he could, trying to stop the grin on his face.  _ Damnit, he’s actually getting to me. This is insane, he’s  _ **_insane._ **

Cas carried them through homeroom and to first period, only adding more to his pile as students dropped off ones they’d found in  _ their  _ lockers. He dropped the entire stack on Dean’s desk, failing to hide the amused expression on his face. “You killed a lot of trees for this.”

“I did. If you say yes they won’t have died in vain.” He sat up straighter and grinned.

“As tempted as I am to give them a valiant end, the answer is still no.” Cas grinned at the pouty look on Dean’s face, and allowed himself to consider what Dean might look like if he finally decided to say yes. He quickly came to the conclusion that it would be adorable at worst and breathtaking at best, which made changing his answer at once both impossible and almost physically necessary. 

_ Maybe I’ll say yes next time just to see it, and then take it back.  _ He shuffled back to his own seat and plopped down, rolling his eyes at himself.  _ That’ll never work. I can already tell that if I ever do say yes… it won’t be something I’m willing to take back.  _

_ Too bad I’ll never know… right? _

**Notes for the Chapter:**

> The next three chapters will be up tomorrow!


	4. The Rumor

**Dean**

Dean was actually happy it was the weekend. Wooing Cas had become a full time job and believe it or not, Dean cared about his grades. He spent Friday night studying and getting his homework done and when he woke up on Saturday, he actually missed Cas. 

**Dean:** **_miss me yet?_ **

He chuckled as he hit send, knowing damn well Cas didn’t miss him, and then went downstairs for breakfast. Dean didn’t even bring his phone with him, because he was 90% sure Cas wasn’t going to respond. 

“Morning, jerk.” Sam said, before taking a bite of breakfast. 

“Mornin’, bitch.” Dean ruffled his ugly long hair as his mom yelled at him for cussing. “Sorry, Mom.” Sam stuck his tongue out at him as he mouthed  _ bitch  _ at him again and went to make a plate.

“So, you got a prom date, Dean?” John asked as he walked into the kitchen. Dean had specifically  _ not  _ told them prom was coming up. 

“Prom?” Mary started, “how did I forget about prom! Who are you going with?” She was way too damn excited about it.

Dean fought the urge to roll his eyes. “Probably no one. I don’t think I wanna go.” He mumbled and then filled his mouth up, hoping they’d drop it. They didn’t. They spent the next twenty minutes talking about their stupid proms and how important it was, how he’d regret it if he didn’t go. 

Mary walked over to touch his face. “I’m sure you could easily get a date, Dean. You’re a catch.” 

_ Not to Cas.  _ “Harder than you think. I asked someone and he said no.” 

Everyone actually looked surprised at that, and it oddly helped his ego.  _ Yeah, me too, guys. _

“How did you ask?” Sam was grinning like a douche. 

“Over the morning announcements.”  _ And about fifty other ways I’m not gonna say. _

“And he said no? Did he say why?” Everyone was done eating at this point and just sitting around.  _ Don’t y'all got something better to do? _

“I dunno. His brother said I should go bigger, but I don’t know. I’m losing confidence, here.” He admitted.

“Oh, honey.” Mary gave him that  _ mom  _ face. “Do you like him?” 

Dean thought about it before answering. Cas was hot, no question there, but he was also so much more than that. He was funny, nerdy, absolutely adorable when flustered, hard-headed, and  _ goddammit _ was he strong. Cas stood for what he believed in, and Dean knew he’d be the type to call him on his bullshit. Dean  _ needed  _ that. “Yeah, Mom. I really do. You should see his eyes, man… ma’am.” 

She chuckled and pulled his ear playfully. “Then don’t give up. He’ll come around. Show him the real Dean Winchester.”

“You mean the fact that he’s a secret nerd?” Sam teased. 

“Shut up, you’re a nerd too, just a different kind. Speaking of, don’t you have a book to read?”

“Boys,” John interrupted before they got too far. “You got anything else up your sleeve? We can help with a little money if you need some.” 

“Well… have you ever looked into skywriting?” Sam started laughing at him and Dean glared at him. “What? Jimmy said he’d like it.” He felt himself blush.

“Jimmy? Is this Castiel?” Mary asked. “Is Jimmy really okay with that?”

“Yeah. I talked to him before I ever asked.”  _ Kinda. You don’t need those details. _

“Dean, we aren’t going to pay for skywriting. I was thinking something much cheaper, like donuts.” 

_ Pfft. Been there, done that.  _ “Not big enough, dad. What about fireworks?” 

“Dean. Be reasonable.”

“Fine, can I borrow your guitar on Monday? I’ll sing him a song.” 

Mary beamed proudly and nodded at John.

_ Ha! Mom’s the boss around here!  _ “Awesome! Thanks!” 

Dean cleaned off his plate and made his way upstairs to check his phone. To his surprise, Cas had responded. 

**Cas:** **_It’s been less than 24 hours._ **

**Dean:** **_Well that’s not a no, so I think this is a step up. Whacha doin?_ **

He grinned like an idiot and set his phone aside to go grab his dad’s guitar, he needed the practice.

**Cas:** **_Studying, since someone decided to distract me during class all week._ **

**Dean** **_: Who? Want me to kick their ass? ;)_ **

**Castiel** **_: Watching you kick your own ass would be hilarious, so… yes, please._ **

**_Dean: Come watch then_ **

_Yeah, right._ Dean was smiling like an asshole still, but even though he knew Cas would never come, he still held onto hope as he watched those dumb three dots dance around.

**Cas:** **_Maybe next time._ **

Dean sent a photo of his pouty face and then went back to the guitar. He tried putting Cas’ names in a few songs, then tried to write his own - failing miserably - before settling on an ‘are you gonna be my date’ remix of Jet’s ‘Are You Gonna Be My Girl’. 

After a few hours of practice, he texted Cas again. 

**Dean** **_: I think you’re gonna say yes on Monday :)_ **

**Cas** :  **_I highly doubt that, but we’ll see._ **

_ We’ll see. _ Dean grinned at his phone. The promise of maybe was enough to give him butterflies, and that was the moment he realized this wasn’t about some dumb bet anymore. 

Dean actually  _ liked _ Cas.

He wanted to prove to him that he was different. He wanted to hold his hand and dance with him and show him who Dean really was. 

**Dean:** **_Good enough for me, handsome._ **

“That song isn’t gonna do. I need to dig deeper.” Dean grabbed his laptop and started some searching.

He spent the rest of the day playing the guitar, trying to find the perfect song. His mom and dad came in his room on separate occasions to help and had a lot of good ideas, but when he went to sleep he still wasn’t set on a song. 

As soon as he woke up, he texted Cas.

**Dean:** **_What kinda music you like?_ **

**Cas** **_: A little bit of everything, except for country._ **

**Dean** **_: Gods, you’re difficult._ **

**Dean** **_: I got distracted last night and made you a mixtape but you gotta promise you’ll actually listen to it._ **

The mixtape was actually going to be for his car when he started, but once he was halfway through, he couldn’t stop thinking of Cas.

**Cas:** **_I don’t think I even own a cassette player, Dean._ **

**Cas:** **_But… thank you. That was unexpectedly sweet._ **

_ Dammit!  _ Lucky for Cas, Dean had an old-school Walkman and he knew he could trust Cas with it.

**_Dean: Welcome_ **

**_Dean: We’ll make it work_ **

He played the guitar until his throat and fingers hurt, then Mary made him tea and sent him to bed. It wasn’t until Monday morning that he realized the sore throat wasn’t from singing, he was fucking sick.  _ Great... I hope no one asks Cas to prom. _

**Castiel**

Monday morning, the very first thing Cas noticed when he got to school was the lack of a Chevy Impala in the parking lot. Whether he wanted to admit it or not, Cas had been looking forward to seeing Dean. 

He’d spent  _ entirely  _ too much time staring at the picture Dean had sent him. How someone could still be so breathtakingly gorgeous when pouting was beyond him, but every time he looked at the photo, his resolve wavered.  _ Maybe he does like me? Surely he’s not going to all of this trouble for nothing, anyone in their right mind would’ve backed off by now.  _

The day was long, and by third period, Cas knew Dean wasn’t just late - he wasn’t coming. That knowledge weighed heavily in his chest in a way he hadn’t anticipated.

_ Do  _ **_I_ ** _ actually like  _ **_him?_ ** Cas frowned, looking down at his desk in his last class of the day. If he sat back and looked at it objectively… Yes, he probably did. When or how such a thing happened, he wasn’t sure, but he actually did miss Dean. 

When he got home, his mother was making soup. Cas hadn’t texted Dean because Dean hadn’t texted him, but he’d apparently talked to Jimmy. 

“Your boyfriend’s sick, Cas. Mom’s making extra for him, but I can’t take it over there. Will you?”

He shifted nervously, wanting to correct Jimmy’s sarcastic use of the word but also secretly loving it.  _ Will Dean be my boyfriend some day? Is that what he wants? Is that what  _ **_I_ ** _ want? _

Their mom spoke up before he could even answer. “Of course he will. Here, I’ll put some in a container. You should see if you can make him a grilled cheese once you’re over there, they don’t travel well or I’d just send one.”

The thought of making Dean Winchester dinner was too much, and that annoying part of Cas’ brain that tried to convince him this was still somehow a joke was shouting at him. But, Astarte was nothing if not persistent, and Cas knew better than to tell her no. “Yes, Mother. I’ll be back soon.”

She gave him a knowing look that suggested she knew he wouldn’t be, then handed him a bag with the container of soup and some crackers in it. 

Cas drafted a text to Dean once he got in the car, but didn’t send it until he was pulling in the driveway. 

**Cas:** **_Um… this is awkward. Can you come outside?_ **

He waited a moment after sending it and swore under his breath at himself for being weird, then grabbed the bag and made his way to the front door. He was just about to knock properly when it swung open.

Mary was standing in the doorway and yelped in surprise. “Oh. Hello, Castiel. I haven’t seen you in years. How are you?” She smiled knowingly.

“Hello, Mrs. Winchester. I… I brought some soup for Dean.” He held out the bag, blushing furiously. “Could you… would you give it to him for me?”  _ Why am I even here?  _

“Don’t be silly. He’s been in bed all day, come in.” She moved aside and ushered him towards the stairs. “Turn right at the top of the stairs and it’s the last door. Just walk right in.”

He twitched, thinking Dean’s bedroom was probably the last place he needed to be. “Thank you, I won’t be long.” Cas made his way past her and up the stairs, his insides twisting with every step.  _ What if this was all a joke and he laughs at me for coming here? Or worse, what if he doesn’t laugh, and this is all real and I have to stop being so damn afraid?  _

Cas hesitated and knocked quietly on Dean’s door, refusing to open it without confirming Dean was ready to be walked in on. 

“Come in.” Dean mumbled from a distance and from what Cas could tell, he sounded pretty sick.

He took a deep breath and opened the door, taking in Dean’s room for the first time in years. He was laying on the bed, but Cas couldn’t bring himself to look at him yet. Instead, he studied the walls. Dean still had the same Zeppelin poster he’s had all his life, and a few others as well scattered around. There was a guitar next to his desk that was intriguing - Cas had no idea Dean could play an instrument. 

Dean sniffled and chuckled a deep laugh, breaking Cas’ resolve to finally look over at him. 

“Hi.” Cas cleared his throat and held out the soup. “I… thought maybe you were hungry? Are you okay?”

Dean scooted against the wall and rolled on his side to face Cas better. He smiled and patted the edge of the bed, encouraging Cas to sit. “Mmhm. M’okay. Just a cold. How was school?” He sniffled again, and his voice sounded so gravelly and hoarse that Cas was suddenly glad he came - sick Dean was a whole different ballgame. 

He sat on the edge of the bed and unpackaged the soup, smiling softly at Dean. “Sit up, I’m not going to feed it to you.” 

“Why not?” He grinned but complied, sitting up with a groan. “Miss me today?”

Cas was becoming an expert at ignoring the heat in his cheeks, but… he felt he should be honest. “Yes, actually. I think I did.” He popped the lid of the container and grabbed the spoon, deciding to indulge Dean - and himself - just once. He gathered some soup on the spoon and held it out to Dean, tilting his head curiously. “It shouldn’t be too hot.”

Dean actually looked shocked a split second before he leaned forward and wrapped his mouth around the spoon. “I can’t taste it, but I’m sure it’s good.” He sniffled, still wearing that infuriating grin. “I missed you, too.”

“Was this your plan all along? Skip school with a cold, make yourself vulnerable and adorable, and lure me here? Was this how you were going to get me to say yes?” Cas handed Dean the rest of the soup, realizing that feeding him was entirely too intimate for his own good. 

“Wait, you think I’m adorable?”

Cas blinked, his face going slack as he realized he’d actually said all of that out loud. He flicked his eyes between Dean’s and swallowed, then distracted himself with trying to get the crackers out of the bag. “I’m not  _ blind,  _ Dean.”

“As  _ adorable _ as your glasses are, I’m glad you’re not blind.” Dean sipped some soup and groaned again. “And to answer your question, no. This wasn’t my plan, actually, it kinda ruined my plan.”

“Well, then,” Cas said quietly. “I suppose you need to get better, because if I’m being honest… I’m kind of curious about what you’re going to come up with next.” 


	5. The Soup

**Dean**

Dean stared at Cas in awe. He couldn’t believe he actually came here with soup. Yeah, Astarte made the soup and told him to come, but Jimmy could have easily done it. 

Cas sure didn’t hate him anymore.

“Thanks for the soup, but I’m not telling you my plan. I still have a few up my sleeve, Novak.” He ate more soup, wishing he could taste it. “You really don’t have a cassette player?” Dean met his eyes, allowing himself to get lost a few seconds before returning to his soup.

“I haven’t needed one in years, so I doubt it. Did you seriously make me a mixtape?” 

“Yeah, you can take my walkman but you have to promise to listen under the stars tonight.”  _ Fuck, that was cheesy.  _ He felt himself blush and went back to eating his soup.

Silence stretched for a moment, but it wasn’t awkward. Cas eventually leaned a little closer, shifting so more of his body was on the bed. “I should… let you get some rest.”

“I slept all day. What if... nevermind.” He finished the soup and set the bowl aside, his body brushing Cas’ slightly when he leaned.

“What if… what, Dean?” Cas looked at him, and Dean could swear the guy was barely breathing. “Tell me.”

“I was gonna say we could watch something... and I promise not to ask you to prom.” Dean’s eyes dropped to Cas’ lips accidentally and he forced them back up to his eyes.

Cas glanced at the door and then back at Dean, nodding quickly. “Okay. I shouldn’t stay long, I have a test tomorrow, but… maybe one wouldn’t hurt.”

Dean smiled and climbed out of bed to grab his DVDs and shuffle through them. “I got all the good ones, in the mood for anything specific? I already binged 4-6 of Star Wars and I hate 1-3.” He sniffled and walked back over to sit with Cas on the edge of the bed.

“How about this one?” Cas pointed to  _ All Saints Day IV: Hatchet Man Lives.  _ “I don’t think I’ve seen this one yet.”

“You’re awesome.” Dean was impressed and jumped up to put it in. He returned to his spot by the wall, leaning against the headboard and patted right next to him. “Get comfy.”

His movements were still hesitant, but Cas toed off his shoes and climbed up next to Dean until their shoulders were touching. The movie started and Cas bit his lip, clearly not a fan of scary movies despite the fact that he was the one that picked it. 

Dean chuckled and pulled up his blanket to cover their legs. “Nervous, Cas? It isn’t that scary, just... slasher.”

“I’m not scared, Dean.” His voice was steady and sure, but Dean didn’t miss the way his body curled to touch him in more places. “It’s just a movie.”

“Mmhmm. I told you, I’m Batman. I’d protect you.” He didn’t wanna push Cas, but he couldn’t fucking help the flirting.

Cas nudged him, humming quietly. “Does that make me Talia al Ghul?” 

Dean laughed and had to hit his chest when a coughing fit hit. “Do you wanna be?”

“Cover your mouth, you’re a child.” Cas gave him a grossed out look but didn’t move a muscle. “She was a constant thorn in Batman’s side, so… I suppose it would be accurate. But they never became serious.”

“I think I’m more the thorn in your side, so maybe you can be Batman and I’ll be Talia.” Dean licked his lips and looked at Cas’ again. The urge to kiss him was overwhelming, but this wasn’t the time or place. He didn’t want to get Cas sick.

Cas looked at him, sucking in a quiet breath at how close they were. “They still… didn’t work out. Then again, Batman never settled down at all.”

“That gonna be you, Cas? Forever bachelor. Cause that won’t be me.” Dean’s always wanted a boyfriend, he’d just never had a relationship make it past a week. “Or at least, I hope. People tend to get sick of me.”

He shifted, pulling his knees up to his chest and looking back at the tv. “If it is me, it won’t be by choice. Jimmy tends to get all of the attention... you notwithstanding, of course.” Cas exhaled hard and closed his eyes. “I’ve never even kissed anyone, and it’s not for lack of trying. The closest I came... he thought I  _ was _ Jimmy.”

“What?! That dude was fucking blind... and stupid. Jimmy looks like the Walmart brand of you.” He wanted to reach out but decided to keep his sick hands to himself. “It’s okay not to have kissed anyone, you will when the time is right.”

Cas suddenly looked nervous, kinda like he had the first time Dean asked him to prom. “I should go, you need rest. Thank you for… the movie.” He scrambled off the bed, slipped on his shoes, and grabbed the container, stuffing it back in the bag. 

“Nah, thank you.”  _ Goddammit. _ “Drive safe, Cas.”

He nodded once, seemingly rooted to the spot, then took off out the door without another glance back. He could hear his mom talking to him briefly and then the sound of the front door shutting. 

Just as the sound of Cas’ shitty car reached his ears, his mom cracked open his door and poked her head in. “That was nice of him.”

Dean sighed and turned off the TV. “Yeah... it was. I’m getting real mixed vibes from him Mom, maybe I should just stop?”

She frowned, coming in and sitting next to him. “This might be a stupid question, but… have you tried telling him you actually like him?”

“I think so?” He scratched the back of his head and thought about that.  _ Maybe I didn’t. _ “I dunno. I thought all this effort would show him.”

Mary smiled sadly at him like he was some kinda lost cause. “In some cases… words speak louder than actions. If you ask me, he’s crazy about you. He’s just scared. Show him he doesn’t need to be.” She patted his knee and stood back up, heading for the door. “Take your medicine and sleep on it, okay?”

“Alright. Night, Mom.” He laid there a while, thinking about ways to  _ tell _ Cas rather than show him, and kept coming up short. Dean never had been good with words. 

**Castiel**

Cas spent that night thinking about Dean… his lips, his eyes, his hands… all of the ridiculous gestures.  _ No one has ever showed me this much attention, and I doubt anyone ever will again. Maybe I should say yes? He said he understood that I’ve never kissed anyone, so… maybe I’m worried about nothing?  _

He tossed and turned, mulling over the potential consequences to saying yes.  _ He’ll know he actually got to me and that I  _ **_do_ ** _ like him, despite all of my insistence that I don’t. People will talk… about both of us. He could be pranking me, and saying yes would be playing right into it.  _

It was impossible to shake that last thought, but at the end of the day… Cas wasn’t going to let that slim possibility stop him. He fell asleep, knowing damn well that the next time Dean asked - if it happened at all and he hadn’t already missed his chance - he was going to say yes. 

Tuesday morning, the Impala was back in its normal spot, but no further promposal came. Dean waved at him in the hallway and stopped for small talk in the halls, but not  _ one  _ word about the dance. He found himself becoming more disappointed each time. 

The rest of the week passed exactly the same. They texted, stopped each other in the halls, Dean even switched seats with Jimmy in History - but still. No talk of prom. 

Cas nearly asked about the sudden switch on more than one occasion but couldn’t bring himself to do it - it was clear he  _ had  _ missed his chance, and now… all he could do was just be happy he gained a friend.  _ A friend I’m crazy about, and now I can’t go back from that. He’ll never again be the meathead I’ve always seen him as, and now I just… have to live with it.  _

Friday night, Astarte called him downstairs to ask for his help with dinner. She told him to set an extra plate, but wouldn’t tell him why beyond that Jimmy was having a friend over and she supposedly couldn’t remember who. 

_ Yeah, right. Probably one of his dumbass girlfriends. Great, I get to spend dinner watching them suck face.  _

She’d pulled out all the stops with a roast, and when it was finally ready, Cas was interrupted by the doorbell as he was bringing the food to the table. 

“Will you get that, sweetie?”

_ Where the hell is Jimmy? Why can’t  _ **_he_ ** _ get it? It’s his damn girlfriend.  _ Cas glared at nothing as he made his way to the front door and swung it open, his breath catching painfully in his throat as he saw who was standing there. “...Dean?”

“Hey, Cas. Pie?” He held it out with a wide toothless grin. Cas could tell it was cherry by the filling in the middle of a cut-out heart, and of course the pie had ‘Prom’ written in crust across the top. Dean had to have baked it himself.

Cas nearly said yes right then, but the uneasiness he’d felt during the week wouldn’t go away. “You… you’re Jimmy’s guest.” He took the pie and stepped aside, staring at the craftsmanship. “I didn’t know you could bake.”

“No, I’m a guest of  _ all  _ of you, and to be honest Cas... there’s a lot you don’t know about me ‘cause you haven’t asked.” He walked past Cas like he owned the place and hugged his parents.

Something unidentifiable pulsed through Cas as he watched Dean integrate seamlessly with his family. It felt a little like longing and a lot like suspicion, but he chalked that last bit up to lingering fear that all was not as it seemed. 

He took a few, timid steps forward and skirted around Dean and his father, setting the pie on the counter. 

Dean glanced his way and bit back a smile. “So... has Cas told you guys I asked him to prom?”

“No, he hasn’t! Dean, that’s wonderful! Congratulations to both of you.” Astarte grinned, heaping a mountain of potatoes onto Dean’s plate.

Cas could’ve died of embarrassment at the look on Dean’s face. “I… didn’t say yes.”

“Nope. In fact, he’s said no about... Oh, I don’t know, fifteen times.” Dean thanked her for the food and met Cas’ eyes again.

Even his dad looked offended. “Castiel, why’d you say no? Dean seems like a nice boy, and you’re always so lonely. Seems to me you’re doing it to yourself.”

This time, the color drained from Cas’ face, and he found himself getting defensive quickly. “I’m not lonely, Dad. And I said no because… because…”  _ Because something isn’t right here, I just don’t know what it is.  _ “Dean is notoriously insufferable, arrogant, and wouldn’t know sincerity if it bit him in the ass. He asked me to prom over the loudspeaker… and prefaced it with the word  _ testicles.  _ If that wasn’t enough, he handed out fliers to half the school.” 

Dean blushed and looked down at his plate. “That was when I was still getting to know you. Now I know not to do it that way.”

“That pie isn’t over the top, it’s one of the sweetest things I’ve ever seen. Just say yes, Cas.” Astarte was smiling sweetly, looking between them like they simply needed a nudge in the right direction. 

He felt cornered, caged. Two things that were very dangerous for someone like Cas. He stabbed a piece of roast beef with his fork and bit it almost violently. “Can we just eat?”

Dean dropped it after that and started eating, avoiding Cas’ gaze most of the night. Once Jagger brought up football, they were all distracted enough, and Dean hung out longer than Cas thought he would. 

When he finally stood up to say goodbye, he finally looked over at Cas. “Cas... will you walk me out?”

Everything in him wanted to say no, but there was something about the look on Dean’s face that had him nodding. “Of course, Dean. Let’s go.”


	6. The Kiss

**Castiel**

The second they were outside, Dean shut the door behind them and Cas crossed his arms, hugging himself. “I’m assuming you didn’t call me out here just to make sure you made it to your car safely?”

“You’re my Batman, remember?” Dean teased, then pulled him in for a hug. “Why are you so grouchy?”

He tensed at the sudden display of affection, but Dean was… warm, and solid, and… “You smell amazing.” Cas relaxed in his arms, burying his face in the crook of Dean’s neck to hide the redness in his cheeks that had blossomed at his admission. “I’m sorry. I don’t like being cornered.”

“You smell amazing, too.” Dean released him and stepped back. “Is that what I’ve been doing to you? Cornering you?”

Cas felt the loss immediately. “Honestly? Not exactly, but… I hate attention, Dean. I hate it, it makes me defensive and… well, you’ve seen how well that’s gone for both of us.” He shifted on his feet, already feeling like shit for what he’d said inside. “You’re not insufferable. You’re absolutely arrogant, but… not insufferable. I shouldn’t have said that.”

“I know. If you thought that, you would have told me to fuck off, but you never did. Arrogant? I don’t have an argument there.” He shrugged and leaned against the door. “But I like you, Cas. I know I haven’t said the words before so... I wanted to.”

Those butterflies made a permanent home in his gut as he watched the way the soft beam from the porch light cast perfect shadows over Dean’s face.  _ This can’t be real. He didn’t just say that.  _ “But why? Why did you decide all of a sudden, after years of barely noticing I existed despite being best friends with my  _ twin…  _ have you decided that I’m someone worth all this effort? It doesn’t make sense, Dean.”

“Well I was...” He stopped and then averted his gaze. “I wasn’t ready for anything then... I am now.”

All of a sudden, Cas knew in his chest that this was it. He was about to have his first kiss, and it was  _ Dean Winchester  _ of all people. The one person at Brinetide that he had no business kissing. The one person who had been so close and yet  _ so  _ far his entire life. All he had to do… was let it happen.

Cas took a terrified step forward and swallowed so hard it was audible. “And what, exactly, are you ready for?”

“I don’t know,” He looked down. “Something more... You.” Dean met his eyes and licked his lips.

The world around him narrowed until all Cas could focus on was the shaking of his own hands and the beating of his own heart. He closed the distance between them but couldn’t bring himself to move forward those final couple of inches.  _ Come on, Dean. Finish it. I can’t.  _ “Oh? Then prove it.”

Dean leaned in and paused, barely whispering. “Okay, Cas.” He closed the distance and pressed those soft, pouty lips to Cas’.

He was inexperienced and he knew it, but  _ damnit  _ it felt good. Cas let out a soft noise, fisting his hands in the side of Dean’s flannel. He pulled back, his heart skipping beats. “Can we… can we try that again?”

“Mmhmm.” Dean leaned in again, this time taking a little more control. Cas could feel he didn’t want to be pushy and was holding back.

He opened for Dean, not entirely sure what to do from that point, but he knew he wanted  _ more. _ Cas wanted to taste every inch of that mouth, he pressed his tongue in and moved closer until Dean was pinned against the front door. 

He felt Dean’s lips turn up in a smile just before he licked into Cas’ mouth, his hands gripped Cas’ hips and held him close. It was very obvious this wasn’t Dean’s first kiss, because he knew  _ exactly _ what he was doing when his hands roamed down to the small of Cas’ back, dangerously close to his ass.

Cas wanted more, he wanted it  _ all,  _ and he wanted it with Dean. He reached behind him, grabbing Dean’s hand and sliding it lower, then fisted his own hand into Dean’s hair and got a little… needy. He moaned into his mouth, delving deeper, aware but not caring at all that his technique was shit.

He felt a flame in Dean ignite as he gripped Cas’ ass and flipped them, pressing Cas to the wooden door and slipping between his legs.

“Dean…” Cas gasped, so hard in his jeans he could barely think straight. He held him close, unwilling to let go but knowing they needed to stop before things got out of hand. “You know I’m still not saying yes, right?”

Dean hugged him and buried his face into Cas’ neck. He huffed a laugh and placed one soft kiss against the skin below his neck, and then moved to step away. “I know. I’ll win you over.” He winked and descended the porch steps. “Sleep good, Cas. See you Monday.”

That seemed like entirely too long, and Cas wasn’t sure if he’d make it three more days. He needed more of Dean like he needed water or the answers to the following week’s Calculus test, but he knew that most people, experienced people, didn’t get clingy after one kiss. They shouldn’t get clingy at all.  _ Damnit.  _

He watched the Impala drive away and stayed on the porch for a couple of extra minutes, until his erection had ebbed enough that he could face his family with a normal expression. 

When he opened the door, he found all three of them standing there with expectant faces. Jimmy spoke up first. “Did you actually just kiss that asshole? On our  _ porch?” _

Astarte was beaming, and Jagger was standing between them looking awkward. Cas smiled, unable to help it. “Yes, I did. But… I’ll have you know I’m  _ still  _ not going to prom with him.”

Jimmy  _ whooped  _ like that was the best news he’d ever heard, but Cas didn’t have the energy to try and work out why his twin was being such a weirdo. He ignored his mother’s continued questions and made his way up to bed, grinning so widely he thought he was going to do permanent damage to his face. 

_ I just  _ **_kissed_ ** _ Dean Winchester!  _

**Dean**

Dean pulled into his driveway with a smile so wide his cheeks hurt. He fucking liked Cas... he actually liked  _ everything  _ about Cas, especially his insistence to stand his ground.

It was fucking admirable. He pulled out his cell phone and sent Jimmy a text. 

**Dean:** **_Bet’s off, you win._ **

And he didn’t even care. The bet didn’t matter anymore, nothing mattered but making Castiel friggin Novak his damn boyfriend. 

Dean walked in his house and was happy no one was around. He didn’t feel like talking about it and if anyone took one damn look at his face they’d see he was  _ way _ too happy and he’d have to explain. 

It took everything not to text Cas right away. He didn’t wanna bug him, and to be frank, he had something to take care of.

Kissing Cas had Dean so turned on, he nearly yanked it in the Impala, - but that seemed entirely too creepy - so he quickly jumped in the shower to take care of that.

It technically wasn’t the first time he thought about Cas while jacking off, but it was the first time since middle school and now he knew how it felt to kiss Cas.

_ That kiss... _

_ That ass... _

_ That... everything. Literally everything.  _

_ Dean was falling for Cas. _

_ Nope... not going there. Back to that ass... _

Dean wanted so much more... he wanted to... “Ah fuck!” He came entirely too fast down his drain and had to laugh at himself. “Geeze, Cas.” 

By the time he collapsed on his bed for the night, he was still smiling, but he wasn’t about to go to bed without saying goodnight to Cas.

**Dean:** **_You’re amazing, Cas._ **

He noticed then that he’d gotten a response from Jimmy. 

**Jimbo:** **_Finally realized there’s nothing you can do to get him to say yes, huh?_ **

**Jimbo:** **_But you better have fucking meant that kiss, Winchester. I’ll kick your ass if you didn’t._ **

While he was contemplating how to word what he needed to say to Jimmy, Cas texted back. 

**Cas:** **_Funny, I was just thinking the same thing about you. I’ll admit… I was wrong about you, Dean. I’m sorry I judged you._ **

He decided to text Cas, Jimmy could wait.

**Dean:** **_It’s okay. I’m still wounded you didn’t listen to that mixtape like I asked but... that kiss helped. Maybe I can kiss you again tomorrow?_ **

Dean hit send with a blush, not understanding why Cas made him more nervous than anyone.

**Cas:** **_Do you promise to go one full day without asking me to that stupid dance?_ **

**Dean:** **_Promise :)_ **

**Dean:** **_Can I ask you other things?_ **

**Cas:** **_Hey, look. I’m saying yes for the first time._ **

**_Dean: Won’t be the last time though, promise._ **

**Dean:** **_Cake or pie?_ **

**_Dogs or cats?_ **

**_Classic rock or new age?_ **

**_Do you think the moon landing was a hoax?_ **

**_Do you ever stare at the sky and wonder what’s out there? Really out there? And then feel small._ **

He hit send and then regretted every single thing he wrote.  _ He’s gonna think you’re an idiot! _

**Cas:** **_Pie. Guinea pigs. Classic rock. No? Yes, frequently._ **

Dean was grinning when he responded and started typing promptly.

**Dean:** **_I agree on all those but the moon landing. But I’ll win you over there too, maybe the next time I get you in my room._ **

He hit send and then read it back, realizing he could have said that much less... creepy.  _ Shit. _

**Dean:** **_Or your room_ **

**Dean:** **_Or a living room_ **

**Dean:** **_I’m fucking this up, ain’t I?_ **

It took a stupidly long time for Cas to text back, so long that Dean was half asleep when his phone vibrated in his outstretched hand. He jerked, squinting at it. 

**Cas:** **_Jimmy’s being an asshole, so how about your room? Your bed was comfortable._ **

He smiled, happy he didn’t scare Cas away yet, but he was too damn tired to text again and took a chance, hitting call and putting the phone against his cheek. When Cas answered, he could tell he was just as sleepy as he was. “Hi,” Dean mumbled.

“Hello, Dean. You sound adorable when you’re tired.”

“You always sound adorable. I can’t see the screen anymore so I wanted to call and say good night.” Dean closed his eyes and he chewed on his lip. 

Cas laughed quietly. “Goodnight, Dean. I’ll see you tomorrow?”

“Mmhmm. Night, Cas. Sleep tight.” He hung up the phone and plugged it in, already missing him. 

The next morning, his first thought was Cas. He couldn’t believe they actually kissed... and planned on kissing again. Today. Dean jumped up and went to wash up and go find food. 

He felt weirdly nervous about this visit, especially after they talked about how comfortable Dean’s bed was and the promise of kisses. He didn’t want to cross any lines or pressure Cas.

Bugging him about prom was one thing, but he would never actually force Cas into anything and hoped he wouldn’t feel pressured to sleep with him because he had “experience”. Dean rolled his eyes and pulled out his phone.

**Dean:** **_We never picked a time... how about now?_ **

Cas texted back almost instantaneously, putting a smile on Dean’s face. 

**Cas:** **_I’ll be over in ten, but I warn you… I’m staying in my pajamas. It’s too early for actual clothes._ **

**Dean:** **_Same. We’ll get pizza in a bit._ **

The thought of being in pajamas, in bed with Cas, gave him butterflies.  _ Wonder if he’ll cuddle... _

He ran downstairs to let Mary and John know, and was happy she said she’d take care of the pizza for them as long as he kept the door cracked. “But we’re both eighteen and we’re not gonna do nothing.”

She sighed, shaking her head. “Fine. Do what you want, it’s not like you can get him pregnant.”

“Now you’re thinkin’.” Dean offered her an innocent smile and as he walked away, he heard John trying to hide a laugh with a cough. 

It wasn’t until he was walking towards the front door that the thought of actually having sex with Cas crossed his mind, but he quickly forced those thoughts away. It wasn’t time for that yet, and Dean was determined to do  _ this _ the right way.


	7. The Documentary

**Castiel**

Knocking on Dean’s door was one of the most nerve-wracking things he’d ever done. He glanced down at his plain grey T-shirt and blue plaid pajama pants and suddenly regretted his choice.  _ I’m having a bedroom date with Dean Winchester and I didn’t even comb my hair, what the hell is wrong with me? _

It was too late to do anything about, because Dean opened the door with a grin. “Man, you’re adorable. Can I hug you?” He moved aside to let Cas in and pulled him in for a hug.

Once again, Cas found himself melting into that embrace. He nuzzled into Dean’s neck and let out a breath, wondering how the hell he fought this for so long. “Hi, and yes. Apparently, you can hug me whenever you want.”

“Oh, good.” Dean closed the door and led Cas in. He absolutely didn’t comb his hair either, and the sight made Cas smile. Dean was wearing some Scooby Doo pajamas and a white shirt, he didn’t even bother with socks. “Let’s grab some coffee and a couple snacks so we can stay in there all day.”

Having no argument to that, he helped Dean fill up a couple of travel mugs and loaded his arms with snacks. Once they were actually up in Dean’s room and the door was closed, Cas got nervous again. It was the good kind, though, so he ignored the slight trembling in his limbs as he set their haul down and turned to face Dean.  _ Just get the second first kiss over with, things will be easier.  _

He stepped forward, trying to be alluring as he pulled Dean in by the fabric of his shirt until they were flush. “Can I kiss you again?”

Dean nodded and licked his lips. Cas felt his hands slide down the top of his ass as their mouths met again. This one was slow, slower than their first one, but it was heating up by the second. Dean pulled him in even though it was impossible to get closer, and rutted their crotches together, squeezing Cas’ ass with a moan.

It was consuming and incredible and Cas lost himself in it, daring to slide his hands under Dean’s shirt to feel his warm, flushed skin. When they finally broke apart, they were both breathless, and Cas was already half hard in his pajamas. He swallowed, closing his eyes and shifting his hips to hide it. “Is that what it always feels like? Kissing?”

“No.” Dean reached down and palmed himself as he cleared his throat. “No, it’s never felt like that for me.”

Cas smiled, biting his bottom lip and heading over to Dean’s bed. “I have nothing to compare it to, but… I think I’m a fan.”

“Me too.” He grabbed his remote and both their coffees. “Alright, ready to watch this documentary? Nothing like some conspiracy theories after makin’ out, huh?”

_ Okay, I can do this. I can pay attention to this documentary instead of his lips… I can do this.  _ He nodded seriously, taking his coffee and wrapping both hands around it to distract himself. “Yes, I’m ready. If I try to kiss you again, just… shove me.”

“Not a chance, Cas.” Dean leaned over and kissed his cheek, then pressed play with his bottom lip between his teeth.

The noise that rumbled through Cas’ throat would’ve been embarrassing if he hadn’t become so callused to the emotion. He took a long, steady sip of his coffee as the man started to drone on, willing - begging - himself to stop thinking about Dean’s lips. 

He lasted right up until the moment Dean’s fingers started dancing across his back, and all of the self-restraint left his body. He carefully leaned over Dean to set his cup down, making sure that nearly every inch of their bodies were touching in the effort, then stopped so close to Dean’s face he couldn’t focus on a single feature. “That was… good coffee.”

Dean set his cup aside without turning his head and then kissed Cas without warning. It made Cas feel like Dean wanted him just as bad, like this was hard on him too.

“Shit,” Cas breathed, then straddled Dean’s lap and kissed him deeper. He was already starting to get the hang of it, how to slide his tongue across Dean’s bottom lip to get him to open, how to angle his head so they didn’t clash. It felt natural with Dean, natural and…  _ fuck, fuck, fuck! This isn’t the time to get another boner.  _

Dean rutted up into him and slid his hands inside Cas’ shirt as their tongues moved together perfectly, like they had their own secret dance. It was that moment Cas became aware of Dean's boner firmly pressing against the crack of his ass.

As badly as he wanted it, he wasn’t ready, and knew he wasn’t. Not quite, anyway... but maybe he  _ was  _ ready for something in between. He slowed the kiss, running his hands down Dean’s chest and bracing himself for what he was about to do. 

He rolled his hips, making damn sure he wasn’t wrong about Dean being hard, and then kissed down Dean’s neck. Slowly, Cas shifted down, bringing his mouth closer to Dean’s waist with tiny, nipped bites over his T-shirt. 

Dean huffed a deep laugh and ran his fingers through Cas’ hair. “Cas... wait.” He took a deep shaky breath. “Are you... you don’t have to.”

_ Shit, does he not want this? Does he not want me to?  _ He looked up, his face incredibly close to Dean’s crotch. “I want this, but… I’ll stop if you want me to.” 

Dean gripped the sheets and bucked up his hips slightly. “Cas... I want this... I just don’t want you to feel pressured. Even if you didn’t want to, even if you never wanted to, I still like you. But fuck... I want it.” His eyes went down to the not-so-subtle tent in his pajama pants. “I want you.”

That was all Cas needed to hear. He licked his lip slowly and pulled down Dean’s pajama pants, practically salivating at the sight of Dean’s cock. Yet again, he had absolutely no idea what he was doing - but Dean knew that, and Cas had to hope he’d understand. 

He wrapped his hand around Dean’s length and stroked, then leaned forward to lap at the tip. The taste sent a shiver down his spine, and the next thing he knew… he was diving in. 

Cas was painfully hard, pressed against the mattress as he sucked Dean deeper. The taste was unexpected, but incredible, and the sounds Dean was making were even better. He bobbed his head, loving the way his lips were stretched and his tongue slid naturally along the length of Dean’s shaft, and the whole thing turned him on to the point he found himself rutting against the mattress, chasing friction. 

**Dean**

_ Holy shit! Cas is givin’ me a friggin blowjob! Just yesterday he was yelling at me and how he’s sucking my... oh fuck, Jimmy is gonna kill me. Ugh no, don’t think of Jimmy! Think of Cas! _ Dean glanced down and shivered underneath Cas. 

For someone inexperienced, he was sucking the hell outta Dean and it felt like he was really enjoying himself, helping with the guilt. He really didn’t want to take advantage of Cas in anyway, but really, he hadn’t. Both times, Cas made the first move. Dean just wasn’t strong enough to deny him. 

_ Fuck... his mouth... so fucking perfect. _ The way his lips looked around Dean’s length had him leaking into Cas’ mouth. His moan at the flavor had Dean instantly wanting to return the favor. Cas deserved to feel this damn good too. 

“Cas... fuck, it’s so good.” He gripped Cas’ hair but let him have full control of the movements.

The words only seemed to spur him on, he took Dean so deep he pushed past the tightness of his throat until Cas was gagging and pulling back, gasping for air and stroking Dean with the saliva he left behind. He looked insanely fucked out, and when he sucked him back in, Cas was full on humping the damn mattress. 

“Oh shit... shit... Cas...” He couldn’t even get the words out before he was coming inside of Cas’ mouth with a loud groan.

If he wasn’t so blissed out, he would have realized just how loud he moaned, but he was too far gone.

Cas swallowed every damn drop and pulled back, a terrified look on his face that didn’t seem to match what the hell had just happened. He wiped his mouth with the back of his hand and glanced toward the door. “Um… where is your bathroom?”

Dean’s eyes widened. “Are you okay?” He sat up, worried he crossed a line but then noticed the wet spot. “Did you just...”

He looked like a deer in the headlights and refused to make eye contact. “I’m sorry.”

“Don’t be sorry.” Dean shoved his spent cock inside his pajamas and leaned in to kiss him, pulling his gaze up by his chin. “That just means you liked it. I’m glad you liked it. Next time... I’ll get to taste you. Let me get you clothes.” He jumped out of bed and walked over to his dresser and pulled out some boxers and some grey sweats. “Here. Get comfy and come back. Please don’t leave.”

Cas nodded, taking the clothes and quickly disappearing. He came back a couple of minutes later, dry and clean, holding his spunked PJ’s. “I can play the virgin card, right? That’s - that’s normal for a virgin?”

“Yeah it is. You shoulda seen how fast I came last night thinking about that kiss. It’s a normal thing when you really like someone... I think. I’m new at the ‘actually liking’ someone part.” Dean blushed and rubbed his neck.

The distance between them closed quickly as Cas came over to wrap his arms around Dean. “I like you, too. Okay? We can be new at this together.”

“Course.” Dean moved to pull Cas back on his lap. “I’m not good with words. If I say something dumb just tell me, okay? I don’t wanna ruin this.”

Cas nodded, resting his head on Dean’s shoulder. “Okay, Dean. I still don’t really understand any of this, but I’m tired of trying to fight it. You were right, you won me over.”

“Told ya.” He grinned and kissed his lips softly. “If we’re movin’ too fast... just tell me okay?”

Another kiss followed quickly and Cas bit Dean’s bottom lip. “I’m a virgin, not a nun. Don’t worry about moving too fast. I want all of you, Dean.”

“I want all of you, too. Maybe after some pizza you’ll let me return that favor?” Dean didn’t wanna push, he really didn’t... but he wanted Cas. In every way.

“As long as you don’t mind me coming in about eight seconds, yes.” Cas laughed, his cheeks barely tinted pink this time. “I have a feeling your mouth is going to be a little more  _ convincing _ than your mattress.”

“I hope so. And no, I don’t mind. I wanna taste you. Was it okay? I was gonna warn you, but couldn’t get it out.”

Another laugh punched outta Cas’ chest. “Yes, it’s not like you warning me would’ve changed anything. If I learned one thing from porn…  _ always  _ swallow.”

“Porn, huh?” Dean wiggled his eyebrows playfully. “You gonna show me the type of porn you like?”

Again, he blushed. “Maybe.”

Dean smiled and kissed him again. “I can’t get enough of you, Cas.” 

He could feel Cas’ grin against his lips a split second before he dove in for more. 

_ Knock knock. _

_ Shit!  _ Cas practically flew off Dean’s lap onto the bed next to him just before his room door opened a crack. “Pizza is here, boys. Are you decent?” 

Dean blushed at that. “Course, Mom.”  _ We already finished. _

Mary pushed inside and Dean knew by one look she had heard him. It made it difficult to meet her eyes.  _ Oops.  _

“Here you are. Plates and napkins are right on top of the box. Be good in here.” She gave him a knowing look and left the room.

“Does she know?” Cas rushed out with a worried tone.

“Nah. It’s fine, I’m sure she has no clue.”  _ Yeah fucking right.  _ “Ready for some pizza?” Dean hopped up and grabbed them some slices. 

Normally, Dean could put away half a pie all by himself, but not today. Today, all he wanted was Cas. After three slices each, they were back on the bed, making out.

It really didn’t take much for them to get hard, and Dean rutted their clothed cocks together a few moments before kissing his way down Cas’ body. “My turn, baby. You sure you’re okay?”

Cas’ eyes closed and Dean could tell he liked that term of endearment, he nodded feverishly to grant permission and Dean didn’t hesitate. 

He pulled his sweats and boxers down in one swift moment and took his first look at Cas’ cock. It was fucking impressive. Dean didn’t expect him to be small or anything, but he didn’t expect his mouth to instantly water.

Precome was already leaking out as Cas squirmed and struggled to keep his eyes on Dean, but he was happy Cas was watching as he licked up his shaft. 

Dean moaned, wanting Cas to know he liked his flavor and then slid his length into his mouth. He kept his eyes locked on Cas, and was  _ not _ disappointed. 

He looked absolutely beautiful with his flushed cheeks and slack jaw. Dean wanted to see him this way every damn day, but it ended all too soon.

Cas wasn’t joking, Dean only slid his warm mouth up and down his cock about four times before Cas’ hips were already bucking. He didn’t get any words out, but Dean knew exactly when he was going to come. 

To make a show of it, he slid up and stuck out his tongue, jacking Cas off to completion into his mouth and then slid him back down his throat, making sure to clean and swallow every single drop. 

As hard as he was again, Cas looked completely fucked out, and Dean knew what he needed. He fixed Cas’ sweats and pulled him to lay down on his side, wrapping his body around Cas and kissing the back of his neck. “Let’s nap.” 


	8. The Spill

**Castiel**

The following Monday, Cas was walking on air when he entered the school building. He’d spent almost the entire weekend with Dean, going home pretty much only to sleep at night.  _ I wish I didn’t even have to do that.  _

He had hickeys covering the base of his neck and absolutely no desire to cover them up - he wore them like a badge of honor, proud of himself by how far he’d come over the last few days.  _ I’m not  _ **_entirely_ ** _ a virgin anymore, and Dean has been…  _ Cas let out a noise a little too close to a swoon, and quickly looked around to make sure he wasn’t heard. 

No one seemed to be paying any attention to him at all, which was normal - and for once, welcome. He grabbed his things and shuffled to homeroom, tapping his pencil on his desk impatiently as he waited for the bell to ring so he could see Dean again. 

He was early to History, hoping he’d be able to steal a kiss or a hug or  _ something  _ before class began, but Dean strolled in late with an apologetic expression. He looked so damn good that Cas couldn’t do much more than stare at him in awe.  _ That’s mine. Dean is  _ **_mine._ **

The next few classes passed in a blur, and he sat down for lunch trying desperately  _ not  _ to think about the way Dean’s lips had felt around his cock. He couldn’t bring himself to be embarrassed about how quickly he’d gotten off; Dean hadn’t seemed to mind and it was easily the best he’d ever felt, period. 

At least when they’d repeated the favors the following day, he lasted another couple of minutes.  _ If I had to think about dead things to hold off, well… that’s my business. That boy has a mouth made for sucking cock.  _

Cas was pulled out of his daydream by Dean himself, tapping lightly on the table in front of him. “Hey, you uh… you wanna go on a walk with me real quick?”

Going anywhere with Dean sounded like a fantastic idea, so he nodded, shoving another bite of food into his mouth before abandoning the rest to get up and follow him. 

Once they left the confines of the cafeteria, they were more or less alone. Yeah, students walked around and a lot of them glanced their way, but Cas believed they were out of earshot. 

Dean slid his fingers into Cas’ and pulled him along with a happy grin, and Cas nearly died at the feeling of actually holding someone’s hand in public. It felt  _ so _ right, and when Dean finally stopped and turned to face him, Cas traced a line over Dean’s T-shirt where he knew he’d left a bite mark. 

“Hello, Dean.”

“Heya, Cas. I missed you. Can I just give you a ride from now on... when I’m not late?” He chuckled. “I overslept this morning, we talked on the phone a little late last night.”

Cas beamed, nodding. “I’m sure Jimmy will get over it.”

“I’ve been ignoring his texts for days. He yelled at me this morning.” Dean bit his lip and flicked his eyes to Cas’ mouth. “I finally just told him to back off and that I really, really like you. Cause I do.”

_ Please don’t be lying.  _ “I like you too, Dean. I hope that much is obvious after this weekend.” He rocked on his toes, landing again with a soft thud. “Not that I’m complaining, but is there a reason we’re hiding in the hallway?” 

“Well... yeah. I... wanted to ask one more time.” He gripped Cas’ chin softly. “Will you go to prom with me, Cas?”

Slowly, Cas nodded, a smile spreading across his face. “Yes, Dean. I will go to the dumb prom with you.” The expression of joy on Dean’s face was worth it, but the kiss they shared after was even better. Cas was holding onto Dean for dear life as they tried to taste every inch of each other right there in that hallway, only stopping when Jaskier Morningstar’s fat mouth interrupted them.

“Holy fucking  _ shit!  _ Novak finally said yes!”

Dean pulled back with a blush and rolled his eyes. “Back up, peeping Tom!” He moved away to push Jask playfully.

It seemed it was too late, other students were peeking their curious heads around the corner to see what Jask was yelling about, and Cas could hear the whispers from where he was standing. He sighed, shaking his head, not concerned, because he had nothing to hide - he just truly didn’t like attention. 

Dean kissed him again and then got lost in a conversation with Jask about limos and tux colors, and Cas slinked off to go finish his food.

Within minutes, Ares was sitting in front of him. “Is it true? You finally said yes to Winchester?”

Cas blinked at him, surprised to even see him. They had an amicable relationship but they weren’t exactly friends, and he’d never taken Ares to be the nosey or gossiping kind. “Yes, I did. We’re together… I think.” He wasn’t really sure how that worked, they hadn’t verbally made it official but it…  _ felt  _ official. 

“Damnit, Cas. I thought the whole reason you kept saying no in the first place was because you knew?” Ares looked sad, like he was telling someone he cared about that their dog died. 

“Knew what, exactly?” Cas shifted, sitting up a little straighter and narrowing his eyes, looking for any signs on Ares’ face that might clue him in. 

There were none, other than that same, regretful expression. “Look, I hate this. I hate that what I’m about to say is true and I hate that you have to hear it from me, but seriously, man. I thought you knew. Winchester was only asking you to prom because he made a big deal out of the fact that no matter who he asked, they’d agree. Jimmy called him on it and said he knew someone that wouldn’t -  _ you.  _ Dean took the bet, and… well, you kept saying no. I thought you knew,” he repeated. 

So many things made sense at once. Jimmy’s strangeness the morning of the first promposal. The looks Dean was giving him, the shock on his face when Cas had said no. Jimmy’s curiosity. The interest Dean showed in him after years of pretending like he didn’t exist. 

_ I was right all along. He doesn’t actually like me, this was all a bet to him. A joke.  _ **_I’m_ ** _ a joke to him… and I just played right into it.  _

If it were physically possible for a heart to actually break, Cas’ would’ve done it. He was sick to his stomach, thinking about how he’d wasted so many ‘firsts’ on Dean. On someone that didn’t actually give a shit about him at all. 

Tears welled in his eyes as Ares continued apologizing, but Cas didn’t care. This wasn’t Ares’ fault, it wasn’t Jimmy’s fault, it wasn’t even Dean’s fault.  _ It’s mine. It’s mine for believing that someone like Dean could ever like me. Could ever even  _ **_see_ ** _ me.  _

The urge to run was so strong that Cas didn’t even stop to get his books or check out, he dashed out the door and to his car - thankful, for once, that he’d had to drive himself. 

Maybe he’d just  _ keep  _ driving. 

**Dean**

Dean was a little sad Cas walked away while he was talking to Jask, but he wasn’t surprised. Cas didn’t want that kinda attention, and the last thing he wanted was to make him feel uncomfortable. So, he let him go.

Or rather  _ watched _ him go, because that ass was out of this world. 

Jask snapped his fingers in front of his face to get his attention and their dumb prom conversation carried on. 

Dean really didn’t care about prom, he’d much prefer another documentary night with Cas.

“I dunno, J, I think I might just ride with him in my car. He likes my car and he doesn’t like being around a bunch of people. We’ll just meet you guys there. Sup, Jimbo.”

Jimmy walked up and rolled his eyes. “Yeah, yeah. You win.”

“Win what? I called off the bet days ago, asshat. I don’t care about that shit.” Dean already missed Cas and was sick of all the damn questions. 

“Is that a damn hickey?” Jimmy leaned in and pinched the fuck out of Dean’s neck, igniting a wrestling match in the hallway.

The play fight was broken up by Ares, grabbing Jask and scowling at Dean. “You’re a dick, Winchester. We all knew it, but  _ Christ,  _ did you need to hurt him like that? The fuck is wrong with you?”

“Hurt who?!” Dean’s mood was instantly shot. “I didn’t hurt anyone.”

Ares scoffed. “Bullshit, did you seriously think no one was gonna tell him? He likes you, dickhead, any moron can see that. Hope your  _ bet  _ was worth it, pretty sure you made the poor kid cry.” He tugged Jask, starting to walk away. “C‘mon, I gotta clean his tray up and go tell MacLeod he had an emergency.”

“What the fuck are you talking about!” Dean grabbed his arm and turned him around. “I called off that fucking bet. Ask Jimmy! Where is he?!”

A split second’s worth of uncertainty crossed Ares’ face. “Hell if I know. He ran out, he probably went home.” 

Jimmy stepped between them. “He’s my brother and this is my fault, I’m going. Dean, stay here. I’ll... text you once I talk to him.”

“Fuck that. I’m comin’!” Dean walked away and motioned for Jimmy to hurry up. “Come on, man.” He pulled out his phone to call Cas, knowing deep down he wouldn’t answer. “Goddammit, Ares!” Dean fought every urge to punch a fucking locker. 

Things were perfect, and now Cas would never trust him again. Just as they were walking out the door, Ares yelled back, “You did it! Don’t blame me.”

Jimmy growled and pushed his way out, not bothering to hold the door open for Dean. He got into his car with Dean right behind him and slammed the door, glancing over at him. “Pretty sure Ares just confirmed my brother’s worst nightmare. How bad is it? How far did you guys get?”

“None of your business. I’m not putting his personal shit on blast. We didn’t fuck, that’s all I’m saying. I’m winning him back, Jimmy. I was gonna tell him how it all started eventually, but I...”  _ Was falling for him. _

“Whatever. I should’ve never made the damn bet in the first place, I didn’t think he’d ever actually believe you.” Jimmy drove a little faster, taking the last turn before their house kinda sharply.

“Believe me  _ what? _ Jimmy, I actually like him. Why do you think I called off the dumb bet?“ Dean was getting impatient. “I’m not just some asshole, okay? I fucking like him.”

The car stopped in the driveway and Jimmy turned to look at him. “Yeah? Then why didn’t you tell him, huh? Look, I’m not saying I don’t believe you, okay? I know you’re not  _ always _ a dick. What I’m saying is Cas is…  _ Cas,  _ and I’d bet quite a lot that he took whatever Ares said and let it fuel every single one of his insecurities. You fell for him? Great. Go prove it.”

Dean got out of the car and ran up to the door, annoyed that he then had to wait for Jimmy to come unlock it. “Come on. I don’t want him hurting for even a minute more, dude.”

Jimmy opened it quickly and stepped back, giving him a ‘I’m gonna regret this, but go get him’ kind of look. 

He took the stairs two at a time, and then stopped at Cas’ door. He felt like shit. What could he even say to fix this? 

After a few deep breaths, he knocked.

The door swung open to reveal a bleary-eyed, but otherwise defiant-looking Cas. “Have you come to rub it in?”

“No. Come on, just hear me out, please?” Dean walked in before he could slam the door in his face. “Can I explain it all?”

Cas crossed his arms and kept his distance, not making eye contact. “You have two minutes, make it quick.”

Dean sighed and started pacing. “Okay, it started as a bet. I’m not gonna lie about it, okay? It did. They were talking shit about me not having a date, but I didn’t wanna go. I made a dumb comment about how it didn’t matter, I could ask anyone and Jimmy said you’d never say yes, so I took the challenge. I lost the bet on day one when you told me no. That was where it should have ended, but I tried again and again and before I knew it, I actually really  _ did _ wanna go with you. I started to get to know you, and like you, and I told Jim he won the bet because I wanted it over. What we did this weekend? That was just us. No bet, no bullshit. I... like you. A lot. Please don’t shut me out. I was an ass. I’m sorry.”

“I knew. Part of me did, anyway. The whole time, from the first one. I knew someone like you would never ask someone like me just because you wanted to.” Cas scoffed, wiping his face. “That’s why I kept saying no.”

“It was dumb, Cas. But I only never talked to you before cause I thought you hated jocks... thought you hated me.” 

And looking at him then, Dean was getting the same damn impression as before.  _ What the hell have I done? _


	9. The Date

**Castiel**

Every part of Castiel wanted to believe Dean. It would be easy to just buy into it, to melt into his arms, to forget his own insecurities. 

But this was Dean, and he was Cas. 

It didn’t work that way. 

“Well, I’m glad to hear you eventually stopped seeing me as a punchline, Dean, but you’ll understand if this still isn’t the best news I’ve ever heard, nor the greatest compliment I’ve ever received.”

“No... I know. And fuck prom. I don’t even wanna go, okay? You aren’t a punchline, and you sure as fuck deserve someone better than me.” He walked over and took Cas’ hand. “I’m sorry.”

A thousand emotions coursed through him as their fingers laced, and Cas didn’t have it in him to argue. After all, if it  _ had _ just been a joke, it would’ve ended, right? Dean wouldn’t have ditched school to come find him, he wouldn’t be  _ here.  _ His voice came out quieter than he’d have liked, but he was proud of himself for forming steady words at all. “I never wanted to go. But I’d have gone with you.”

Dean pulled him in for hug, like he couldn’t fight it for even a second longer. “I wish I could take it back and date you years ago.”

Cas huffed a laugh, wrapping his arms around Dean and burying his face against his chest. “I don’t. You weren’t exactly boyfriend material back then.”

“I still ain’t. But I’m trying to be.” Dean kissed his forehead. “Will you go on a date with me? A real date, to some fancy restaurant?”

_ Can I? Can I ignore all of it?  _ He curled closer to Dean, knowing it would be harder to let him go than to get over their shitty beginning. He nodded against his shoulder, tilting his head up to lightly kiss the underside of Dean’s chin. “Yes. But I swear to god, if I hear about some homeroom betting pool involving how long it would take you to get me to go on a date, I’ll kick your ass.”

“I’ll let you.” He chuckled lightly. “I swear that’s the whole truth. No more bets. Nothin’. Just you and me.”

Cas let out a shuddering breath, standing on his tiptoes and kissing Dean square on the mouth. No finesse, no heat, just a flat, pressured kiss. “I believe you. Against probably my better judgement, and maybe just because I want to so bad I can’t breathe… I believe you.”

“I’m sorry.” Dean picked him up and buried his face in his neck. “I never meant to hurt you. Wanna punch me?” He stood straight again. “C’mon, right here in the jaw. Go for it.”

As momentarily tempting as that was, Cas didn’t want to damage that perfect face. “I’d rather you just kissed me until I forgot about all of this, but if you’d rather I hit you…”

“Kiss is better.” Dean leaned in to kiss him and lift him up, carrying him to the bed. Cas wrapped his legs around him just as they tumbled down, desperate not to let him go. He rutted up against Dean, trying to ignore the tug on his skin that reminded him he’d shed actual tears. 

Dean pulled away but kept their faces close. “I don’t like that I made you sad.”

“You did. Now quit talking about it. Just kiss me, you’re already failing in your quest to kiss me until I forget it.” Cas sucked in a breath and flicked his eyes between Dean’s, tightening his grip with his legs. “Just make me forget it.”

So he did, he dropped back down and kissed him until they were both hard and grinding together. Cas was more turned on than he’d ever been in his life, and again, he didn’t want to stop. 

He gasped against Dean’s mouth, becoming more insistent by the second. He licked in, scratching Dean’s back under his shirt and pressing their hips together until everything else just blurred. 

Dean started kissing down his neck while his hands roamed under Cas’ shirt. He flicked his nipple and smiled into his mouth. Cas was sure nothing could stop them from going all the way.. until Jimmy knocked.

It took Cas several, frozen seconds to orient himself enough to even say anything. When he did, his voice came out wrecked. “Go away! We’re fine.”

Jimmy pushed open the door anyway and eyed them, leaning against the frame with his arms crossed. “Yeah, no. Sorry, guys.”

Dean scuffled off of Cas and sat next to him. “The hell Jimmy.” He blushed and covered his boner. “We talked it out.”

“Bet you did. Still doesn’t mean I’m gonna let you steal my brother’s v-card right after something like that.”

Anger flared through Cas and he sat up, not bothering to hide his own erection. “In case you didn’t notice,  _ James,  _ I’m only in this mess because  _ you  _ played me like a pawn. I’m just as old as you are, I can make my own decisions. Now get out.” He stood firm, even if he knew Jimmy was technically correct. This wasn’t the right time, and certainly not the best circumstances… but he was tired of Jimmy trying to speak for him. 

Jimmy held up his hands and backed away. “Fine, Castiel. Dean... don’t fuck this up.” He turned to leave and the mood was already gone, but at least they were going in the right direction.

“Sorry. He’s right... I wanna do this right. You deserve so much, Cas.”

It was probably going to take a while for Cas to truly believe that Dean meant it, but he owed it to both of them to at least find out. So what if the entire thing had started with a bet? People had stranger beginnings to their love stories, and now that the truth was out and Dean was still there… maybe he could finally get his. 

Cas kissed Dean again, gently this time, and then curled up with his legs crossed on the bed. “So… where are we going on our date?”

**Dean**

Dean had been on a simple dinner and a movie thing before, but never one like this - not even close. Cas was fucking incredible and their date couldn’t be anything less. 

His parents would occasionally go to some fancy restaurant on the rich side of town called Bela’s. It looked like some uppity place they had no business going to, regardless of the fact that they both dressed up a little.

Cas looked amazing in his white dress shirt and black slacks. Dean felt like a loser next to him in some too-tight dress pants, but Cas seemed to like what he saw.

Dean decided to be the perfect gentleman tonight. He knew the food would suck and he’d probably leave starving, but he needed Cas to see how special he was.

It was one of those places where you needed to wait to be seated, and the hostess eyed them like neither one of them belonged there. Cas, surprisingly, turned on some charm Dean didn’t know he possessed to get them a better booth, and he had to admit it had a helluva view. 

“This place is… rigid, I feel like I’m at a baptism or something,” Cas whispered. 

“Ugh...” He almost slipped, and cleared his throat. “Not that bad. Let’s check out this menu.” He looked down at the row of utensils and frowned. “Why are there so many? This isn’t the Titanic.”

Cas huffed a laugh and tilted his head, nodding down at them. “There’s a salad fork, a regular fork, a soup spoon, a regular spoon, a steak knife, and… a butter knife. Though, I wouldn’t put it past this place to start playing that awful Celine Dion song.” 

“Ah, Jesus.” Dean pulled at the collar on his shirt. “Alright, let’s check this menu out.”

They spent a moment looking over the ridiculous choices, and the next thing Dean knew, he could feel Cas’ socked toe trying to slide under his slacks to brush his ankle.

Dean grinned, keeping his eyes on the stupidly-portioned food. “Seriously, who could get full off this shit? My parents are ridiculous.” He whispered.

Cas cleared his throat and reached over to take Dean’s hand. “Dean… this place… it’s not us. You don’t have to be something you’re not to impress me, okay? I don’t think I like it here anymore than you do. Why don’t we go down to Porky’s and see which one of us can eat a double-bacon cheeseburger faster?”

“Goddammit, I think I love you.”

The smile splitting Cas’ face was worth the potentially too-early confession. He nudged Dean, muttering ‘shut up’ under his breath, which only made Dean mean it even more. 

They waved smugly to their waitress as they passed her, and raced out to Dean’s car, running hand in hand like they’d just ‘dined and dashed’. 

Porky’s wasn’t that far away, so at least they didn’t have to wait too much longer to get actual food. Dean was  _ starving.  _

He pulled Cas right to his favorite table and sat next to him this time, scooting their chairs a little closer so Dean could drape an arm around him. “This okay?”

Cas molded himself to Dean’s side and nodded, quickly kissing his jaw. “I already feel more welcome here, and I’ll never complain about a chance to be near you. We should’ve just  _ started _ here.” 

“I know that, I’m sorry. I just felt so damn bad after that whole ‘bet’ thing that I wanted to make it up to you. My dad kept telling me that’s the restaurant he takes my mom to when he pisses her off, so I figured it wouldn’t be that bad.”

A soft chuckle worked its way out of Cas, and the sound eased some of Dean’s anxiety. “Well, I’m not your mother, Dean. You’ll always have better luck keeping things simple with me.” 

_ Yeah, I think I’m starting to get that, and it’s more than I ever coulda hoped for.  _ “So, it’s probably a good thing my skywriting idea got vetoed, huh?”

Cas looked horrified, and it was one of the cutest damn things Dean had ever seen. “I don’t even want to know what that means. But now that I know how this all started… I’m assuming Jimmy put you up to the grand gestures?”

“Yeah, how’d you guess?”

“Jimmy knows me better than anyone. If he wanted me to say no, telling you the ‘bigger the better’ was a damn good way to do it.”

They’d opted to share one of the best milkshakes in town, and this waitress smiled like she was watching a bunch of puppies fall all over each other when she handed them two straws and they both went at it at once. The whole atmosphere was different than it was at Bela’s, and it felt… more right than anything else in his life ever had. 

Dean won the burger-eating contest hands down, but took the very delicious opportunity to lick up the ketchup and mustard Cas had gotten all over his face. From the way Cas was smiling, they  _ both  _ won that round. 

There was suddenly something Dean desperately wanted to see, so he angled his body to face Cas fully and bit his lip, knowing how insane that usually drove people. “You’ve  _ got _ to have the prettiest eyes I’ve ever seen, y’know that?” 

Redness splashed across Cas’ cheeks, and Dean nearly cheered. He’d finally -  _ finally  _ \- made Cas blush for something other than embarrassment. 

“You’ve got the prettiest  _ everything  _ I’ve ever seen, does that count?” Cas came closer and brushed their noses together, and Dean was damn sure his skin now matched his date’s. 

“Yeah, yeah. You gonna eat those fries?” Dean jerked his chin toward Cas’ plate and grinned like an asshole when Cas pushed it toward him. “Oh yeah, we’re gonna get along  _ juuust  _ fine.”

From there, the conversation was so easy it almost couldn’t be real, and Dean nearly dropped to his knee right then to propose when Cas ordered them an entire friggin pie to go. 

_ How I never saw you before, I’ll never understand… but I see you now, and I’ll do whatever I can to keep proving that to you as long as you’ll let me.  _

And hell, maybe one day, he’d even say all of that out loud.


	10. The "Prom"

**Castiel**

Since the day things blew up, his relationship with Dean had been solid. They’d made it official, dealt with all the assholes at school that decided they had something to say about it, and spent some time with both of their families. 

But for one reason or another, they still hadn’t had sex. It was the one and only line they  _ hadn’t _ crossed. The weekend before, Dean had obliged one of Cas’ porn fantasies and they’d frotted with Dean caging Cas against the wall. To say it was everything he hoped it would be was an understatement. 

The morning of prom finally came around, and Cas was nervous. It had been hyped up so much in his time with Dean that he was afraid to even go, which was something he finally confessed to Dean after they were both completely dressed and had put up with both of their mothers taking a thousand pictures. They made it as far as the car before Cas grabbed Dean’s arm. “Can we… I mean, would you…” He huffed, shifting on his feet and steeling his nerve. “I don’t think I want to go to prom. I never did.” 

“I know, baby. We’re not goin’.” He grinned and kissed his lips. “I have something else planned, and that dumb dance damn near bought us the entire night.”

The relief flooding through Cas was unreal. He loosened his tie but left it on, then slid into the passenger seat. Once Dean was in, Cas glanced at him curiously. “Where are we going?”

“You’ll see.” He started the car and slipped in a cassette with a grin. “This is your mixtape. And... leave that tie on a little longer. I wanna be the one to take it off.” Dean winked and put the car in drive.

Cas was having a hard time deciding what to concentrate on, the implications of what Dean had just said or the song coming out of the speakers. All he really knew was that if he didn’t  _ finally  _ get laid that night, he was going to end up tying Dean down in a motel room somewhere they couldn’t be bothered and just riding him. He wanted him so badly it was almost physically painful. 

The song was beautiful, some classic rock number Cas kind of recognized but wasn’t sure he really  _ knew,  _ though the rendition Dean was singing was far better, anyway. He reached over to take his boyfriend’s hand and smiled, the warmth of the spring night matching the warmth in his chest. 

Dean sang along, leaning in to kiss Cas’ cheek every so often, and Cas was so entranced he didn’t even realize they were out in the country until Dean hit gravel.

He switched his focus reluctantly to the road in front of them, trying to figure out where they were. All of the city lights had faded out and all Cas could see where stars, thousands of them, dotting the night sky the way the freckles peppered Dean’s face. “Where…?”

“I used to come out here at night and pretend I was at parties and stuff. My parents were never strict, but they didn’t understand me wanting to just drive to the country and stare at the sky. We don’t have cell reception here, and they weren’t comfortable with that, but I still did it.” He pulled off the gravel road onto some grass and put the car in park. “I’ve never brought anyone here... ever. But I was hoping you’d wanna ditch that dumb dance and all those dumb kids for something else. Something just for us.”

Cas nodded dumbly, absolutely awestruck by all that was Dean. “You’re incredible. Did you know that? You say that about me all the time, but you?” He shook his head, curling his fingers around Dean’s. “You’re amazing, and yes, I want this. I want all you have to offer, Dean.”

“Awesome.” He grinned and leaned in for a kiss. “Alright, out. Gotta get the whole experience, babe.” 

Dean got out of the car and rounded to the trunk, pulling out a big blanket and a cooler. “I stole us some beers from my dad’s fridge, but I also brought water and soda... so, no pressure.”

It was already a thousand times better than prom, or any dance, or anything involving other humans. Cas happily helped Dean spread out the blanket and opted for a water - if he was finally going to get laid like he hoped, he wanted to be sober for it. “Okay, whole experience. What’s next?”

“Um...” Dean looked nervous for a second and then walked back to the car to put the music louder. As he walked back, he held out his hand. “Will you dance with me, Cas?”

Nothing in the world could make Cas say no. He gladly, happily took Dean’s hand and stepped forward, not bothering to wipe the grin off his face. “Is there a word stronger than yes?”

“Uhh... nah.” He shook his head with a grin and then spun Cas around slowly. “I meant what I said at that stupid restaurant. I...” Dean licked his lips and met Cas’ eyes. “I fell for you.. I love you, Cas.”

Something seized up in Cas’ chest and he couldn’t hold off long enough to respond, he threw his arms around Dean’s neck and kissed him so hard they nearly toppled over. Dean caught them both and chuckled, and Cas kissed him again before finally composing himself. “I love you too, Dean.” And, not one to miss an opportunity, Cas pressed on. “Does this mean you’ll finally fuck me?  _ Please?  _ I don’t think I can wait any longer.”

Dean pulled his lip between his teeth and closed his eyes tightly, like the idea of not fucking tonight was physically painful for him as well. He nodded, seconds before gripping below Cas’ ass and lifting him up to carry him to the blanket.

They landed with a much softer thud than Cas anticipated, which just further proved how strong Dean was. The stars were exploding behind him, and Cas knew to his core that finally - on the night that nearly ruined everything - he was about to get more than he ever could’ve dreamed of. 

**Dean**

Dean was nervous when he first laid Cas down, but with each passing second, he knew this was right.  _ This _ was how it should be.

They kissed until they couldn’t take it anymore, and though taking their clothes off wasn’t as smooth as Dean would have hoped, it was still absolutely perfect.

Cas’ breath hitched as he laid flat on that blanket, the moon casting shadows over his bare body. “You were right, leaving the tie for you to take off was absolutely worth it.”

Dean bit back a laugh and sat up on his knees to take in Cas’ body. “Fuck, you’re beautiful. You sure you wanna go all the way?”

He nodded quickly, reaching out to flatten his palm against Dean’s chest. “Yes, I’m sure. I’ve been sure. I don’t know why the hell it hasn’t happened already.” Cas’ eyes widened briefly and he licked his lip, squirming on that blanket. “Please?”

“I’ve wanted it, too. I just didn’t wanna pressure you. I think about fuckin’ you every single day.” He leaned down tentatively and shifted Cas, still trying to be gentle. “Can you spread your legs for me, baby?”

Cas’ legs spread eagerly, allowing Dean to slot between them. “I appreciate you not pressuring me, but I don’t want to wait anymore.” 

“I don’t either. I just wanted to feel like I deserved you, and now that I know you love me too, I think we’re ready.” He pulled out some lube from his suit coat and shrugged. “I had hoped tonight would be the night.”

“Don’t most kids get laid at prom?” Cas smirked, sitting up slightly to kiss him again, all eagerness and need. 

Dean kissed back and then clicked open the cap. He squirted some on his fingers and then warmed it up while he watched Cas. “Have you ever... fingered yourself?”

He nodded quickly, bowing his legs out further and gripping his cock. “Yes, but the angle was always weird. And I… I never had any toys or anything.”

“Okay, I just wanted to know if you knew it would burn. I’ll go slow for you.” Dean leaned down and pressed the pad against Cas’ tight hole while he kissed along his thigh.

The mixtape was still playing through the Impala’s speakers, setting the mood just right as Dean slipped that first finger inside and Cas gasped. As he trailed his lips down those lean muscles, Dean knew it was the good kind of gasp, the kind that silently said  _ ‘more’.  _

Dean sucked a mark while he slid his finger in and out. Cas was asking for more before Dean thought he was ready, but he was in no place to deny him. He nudged another finger in and took Cas’ leaking cock into his mouth.

They’d fooled around enough that Dean wasn’t worried about Cas coming too soon, and he absolutely opened up a little easier with the added stimulation. By the time he was scissoring three thick digits inside of him, Dean was leaking all over the damn blanket, and it was hard to tell which one of them wanted what was coming next more. 

His hands were shaking as he finally lubed himself up. This would be Dean’s first time without a condom, and the thought was as exciting as it was scary. But they were clean, and they wanted to experience this first together. Dean lined up his cock and met Cas’ eyes. “If it hurts, just bite me.”

Cas looked confused for a moment and shook his head. “That’s a terrible idea, we both know I’m going to bite you if it feels  _ good.  _ If it hurts, I’ll just… tell you it hurts. Now,  _ please,  _ Dean,” Cas begged, wiggling down to try and urge him in. “I can’t wait another second.  _ Please.” _

He huffed a laugh and pushed the head inside. It already felt so fucking good... better than anything he had ever experienced in his life. “Oh, fuck... Cas... you’re so tight.” He pushed in further with a groan.

Immediately a mess, Cas reached down to squeeze his cock with one hand while the other pulled Dean down so he could kiss him. “More.”

Dean gave him more until he didn’t have any more to give. They both moaned at the feeling, and Dean stayed seated as he kissed along Cas’ neck and chin.

Sure enough, Cas grazed his teeth along the line of Dean’s shoulder and then bit down, sending a shockwave of pleasure and pain through Dean’s body. He rocked his hips on instinct, and the noise it drew from Cas had him doing it again. 

Cas’ ass squeezed his entire length so tightly he never, ever wanted to leave. He slowly slid out and back in, working Cas open with his cock. Dean struggled with words, but even in the throes of passion, he had to know Cas wasn’t in pain. “You okay, baby?” He rushed out in a whisper as he continued to fuck into him.

Heavy breaths scattered Cas’ reply. “Y-yes, I… fuck, that’s… you… yes.” He wrapped his legs around Dean’s ass and bit him again, trailing a line of wet, sloppy kisses over his skin. 

“Good... good... ah, fuck... Cas I’m not gonna last... so... good. Fuck!” Dean wasn’t forming words any better than Cas, but he could feel himself balancing on the edge. He sped up, snapping his hips into Cas and slamming their mouths together in a messy kiss as he filled up his ass for the very first time.

Cas let out a choked-off, low moan, tipping over a moment later. Dean kept moving, unwilling to be done  _ or  _ pull out, until Cas went boneless against the blanket and Dean was slipping out whether he wanted to or not. He kissed over Cas’ face and slid his arm under him to hold him tight. 

“Dean, that…” Cas buried his face in Dean’s neck, his chest heaving. “You’re amazing. That was amazing.”

“Nah, you’re amazing, Cas. I’m a lucky guy.” He kissed his head and relaxed into him, knowing deep down that they were it for each other.

Falling for Cas was kinda like taking a long walk off a short pier - by the time he realized he’d gone over the edge, he was so far past it he could barely see the damn thing anymore. He definitely hadn’t been expecting it when he’d taken that bet, but... isn’t that how all the best things happen?


End file.
